Production Method 1

2927-71-1

954220-98-5

Reaction Conditions

1.1 Solvents: Diethyl ether ,  Tetrahydrofuran ,  1,2-Dimethoxyethane ;  10 min, 0 °C; 1 h, 10 - 15 °C; 15 °C → 0 °C
1.2 Reagents: Triethylamine Solvents: Tetrahydrofuran ;  < 5 °C
1.3 Reagents: Iodine Solvents: Tetrahydrofuran ;  < 15 °C; 30 min, < 15 °C
1.4 Reagents: Hydrochloric acid Solvents: Water ;  pH 1

Reference

Preparation of pyrrolidine-fused thiadiazine dioxide compounds as beta site APP cleaving enzyme (BACE) inhibitors, pharmaceutical compositions, and their use

, World Intellectual Property Organization, , ,

Production Method 2

2927-71-1

954220-98-5

Reaction Conditions

1.1 Solvents: Diethyl ether ,  Tetrahydrofuran ,  1,2-Dimethoxyethane ;  < 15 °C; 1 h, 15 °C; 15 °C → 0 °C
1.2 Reagents: Triethylamine Solvents: Tetrahydrofuran ;  5 °C
1.3 Reagents: Iodine Solvents: Tetrahydrofuran ;  5 °C
1.4 Reagents: Water ;  5 °C → rt

Reference

Structure-Based Design of an Iminoheterocyclic β-Site Amyloid Precursor Protein Cleaving Enzyme (BACE) Inhibitor that Lowers Central Aβ in Nonhuman Primates

Mandal, Mihirbaran; Wu, Yusheng; Misiaszek, Jeffrey; Li, Guoqing; Buevich, Alexei; et al, Journal of Medicinal Chemistry, 2016, 59(7), 3231-3248

Production Method 3

2927-71-1

954220-98-5

Reaction Conditions

1.1 Solvents: Diethyl ether ,  1,2-Dimethoxyethane ;  1 h, < 15 °C; 0 °C
1.2 Reagents: Triethylamine ,  Iodine Solvents: Tetrahydrofuran
1.3 Reagents: Sodium bicarbonate ,  Sodium bisulfate ,  Water

Reference

Preparation of tetrahydropyrrolothiazinamines as BACE inhibitors

, World Intellectual Property Organization, , ,

Production Method 4

954220-98-5

Reaction Conditions

Reference

Thiophenyl-substituted 2-imino-3-methyl pyrrolo pyrimidinone compounds as bace-1 inhibitors, compositions, and their use

, United States, , ,

Production Method 5

1480-99-5

954220-98-5

Reaction Conditions

1.1 Reagents: Phosphorus oxychloride ;  rt → 90 °C
1.2 Reagents: Diphenylamine ;  0.5 h, 90 °C; 5 h, 90 °C
1.3 Reagents: Water ;  < 30 °C

Reference

Preparation of 6-methyl-5-fluoro-2,4-pyrimidinediamine compounds as antineoplastic agents

, China, , ,

Production Method 6

2927-71-1

954220-98-5

Reaction Conditions

1.1 Solvents: Diethyl ether ,  Tetrahydrofuran ,  1,2-Dimethoxyethane ;  < 15 °C; 1 h, 15 °C; 15 °C → 0 °C
1.2 Reagents: Triethylamine ,  Iodine Solvents: Tetrahydrofuran ;  5 °C
1.3 Reagents: Water

Reference

Overcoming Time-Dependent Inhibition (TDI) of Cytochrome P450 3A4 (CYP3A4) Resulting from Bioactivation of a Fluoropyrimidine Moiety

Mandal, Mihirbaran ; Mitra, Kaushik; Grotz, Diane; Lin, Xinjie; Palamanda, Jairam; et al, Journal of Medicinal Chemistry, 2018, 61(23), 10700-10708

Production Method 7

2927-71-1

954220-98-5

Reaction Conditions

1.1 Solvents: Diethyl ether ,  Tetrahydrofuran ,  1,2-Dimethoxyethane ;  < 15 °C; 1 h, 15 °C; 15 °C → 0 °C
1.2 Reagents: Triethylamine ,  Iodine Solvents: Tetrahydrofuran ;  5 °C
1.3 Reagents: Water

Reference

Preparation of phenyliminomethylpyrrolopyrimidinone derivatives for use as BACE-1 inhibitors

, World Intellectual Property Organization, , ,

Production Method 8

2927-71-1

954220-98-5

Reaction Conditions

1.1 Solvents: Diethyl ether ,  Tetrahydrofuran ,  1,2-Dimethoxyethane ;  < 15 °C; 1 h, 15 °C; 15 °C → 0 °C
1.2 Reagents: Triethylamine ,  Iodine Solvents: Tetrahydrofuran ;  5 °C
1.3 Reagents: Water

Reference

Preparation of thiophenyliminomethylpyrrolopyrimidinone derivatives for use as BACE-1 inhibitors

, World Intellectual Property Organization, , ,

Production Method 9

2927-71-1

954220-98-5

Reaction Conditions

1.1 Reagents: Triethylamine ,  Iodine Solvents: Tetrahydrofuran ,  1,2-Dimethoxyethane ;  1 h, 15 °C; 1 min, -5 °C
1.2 Solvents: Water

Reference

Preparation of amine-substituted heterocyclic compounds as EHMT2 inhibitors

, World Intellectual Property Organization, , ,

Production Method 10

1480-99-5

954220-98-5

Reaction Conditions

1.1 Reagents: Triethylamine ,  Diisopropylethylamine ,  Phosphorus oxychloride ;  3 h, 40 °C
1.2 Reagents: Water

Reference

Preparation method of 2-chloro-5-fluoro-6-methylpyrimidine

, China, , ,

Production Method 11

2927-71-1

954220-98-5

Reaction Conditions

1.1 Solvents: Tetrahydrofuran ;  0 °C; 1 h, 10 - 15 °C; 15 °C → 0 °C
1.2 Reagents: Triethylamine Catalysts: Iodine Solvents: Tetrahydrofuran ;  0 °C; 1 h, 0 °C; overnight, rt

Reference

Heterocyclic compound and its composition and application as anti-influenza virus drug

, China, , ,

Production Method 12

2927-71-1

954220-98-5

Reaction Conditions

1.1 Solvents: Tetrahydrofuran ;  0 °C; 1 h, 15 °C
1.2 Reagents: Iodine Solvents: Tetrahydrofuran

Reference

Heterocylic compound as inhibitor against influenza virus and its preparation

, China, , ,

Production Method 13

2927-71-1

954220-98-5

Reaction Conditions

1.1 Solvents: Tetrahydrofuran ,  1,2-Dimethoxyethane ;  < 15 °C; 1 h, 15 °C; 15 °C → 0 °C
1.2 Reagents: Triethylamine Solvents: Tetrahydrofuran ;  5 °C
1.3 Reagents: Iodine Solvents: Tetrahydrofuran ;  < 15 °C
1.4 Reagents: Water ;  < 25 °C
1.5 Reagents: Hydrochloric acid Solvents: Water

Reference

Hexahydropyrrolothiazine compounds as BACE1 inhibitors and their preparation

, World Intellectual Property Organization, , ,

Production Method 14

954220-98-5

Reaction Conditions

Reference

Pyrrolidine-fused thiadiazine dioxide compounds as bace inhibitors, compositions, and their use

, United States, , ,

2,4-Dichloro-5-fluoro-6-methylpyrimidine Raw materials

• 2,4-Dichloro-5-fluoropyrimidine
• 2,4(1H,3H)-Pyrimidinedione,5-fluoro-6-methyl-

2,4-Dichloro-5-fluoro-6-methylpyrimidine Preparation Products

• 2,4-Dichloro-5-fluoro-6-methylpyrimidine (954220-98-5)

• 1. An atomistic mechanism for the degradation of perovskite solar cells by trapped charge?
  Eunhak Lim,Jiyoung Heo,Seong Keun Kim Nanoscale, 2019,11, 11369-11378
• 2. An insight into the role of side chains in the microstructure and carrier mobility of high-performance conjugated polymers?
  Jianyao Huang,Dong Gao,Zhihui Chen,Weifeng Zhang Polym. Chem., 2021,12, 2471-2480
• 3. An integrated process of CO2 capture and in situ hydrogenation to formate using a tunable ethoxyl-functionalized amidine and Rh/bisphosphine system?
  Yu-Nong Li,Liang-Nian He,Xian-Dong Lang,Xiao-Fang Liu,Shuai Zhang RSC Adv., 2014,4, 49995-50002
• 4. An investigation on the second-order nonlinear optical response of cationic bipyridine or phenanthroline iridium(iii) complexes bearing cyclometallated 2-phenylpyridines with a triphenylamine substituent?
  David B. Cordes,Alexandra M. Z. Slawin,Stefania Righetto,Denis Jacquemin,Eli Zysman-Colman,Véronique Guerchais Dalton Trans., 2018,47, 8292-8300
• 5. An approach to the structure and vibrational analysis of cis- and trans-3-chlorostyrene through IR/Raman and INS spectroscopies and theoretical ab initio/DFT calculations?
  J. M. Granadino-Roldán,M. Fernández-Gómez,A. Navarro,T. Pe?a Ruiz,U. A. Jayasooriya Phys. Chem. Chem. Phys., 2004,6, 1133-1143

• Solvents and Organic Chemicals Organic Compounds Organoheterocyclic compounds Diazines Halopyrimidines
• Solvents and Organic Chemicals Organic Compounds Organoheterocyclic compounds Diazines Pyrimidines and pyrimidine derivatives Halopyrimidines

• 137234-74-3(4-Chloro-6-ethyl-5-fluoropyrimidine)
• 137234-85-6(2,4-Dichloro-6-ethyl-5-fluoropyrimidine)
• 5424-21-5(2,4-Dichloro-6-methylpyrimidine)
• 1488852-88-5(4-Chloro-2-ethyl-5-fluoro-6-methylpyrimidine)
• 1416438-39-5(2,4-Dichloro-6-cyclopropyl-5-fluoropyrimidine)
• 898044-55-8(4-Chloro-5-fluoro-6-methylpyrimidine)
• 1240622-52-9(4-chloro-5-fluoro-2,6-dimethylpyrimidine)
• 1192479-36-9(2-Chloro-5-fluoro-4,6-dimethylpyrimidine)
• 134000-96-7(2-Chloro-5-fluoro-4-methylpyrimidine)
• 96819-53-3(2,4-Dichloro-5-fluoro-6-(trifluoromethyl)pyrimidine)