Production Method 1

1844856-75-2

936250-22-5

Reaction Conditions

1.1 Reagents: Butyllithium ,  Triisopropyl borate Solvents: Tetrahydrofuran ,  Hexane ;  -78 °C
1.2 Reagents: Hydrochloric acid Solvents: Isopropanol

Reference

Development of an Efficient Synthesis of (2-Aminopyrimidin-5-yl) Boronic Acid

Patel, Nitinchandra D.; Zhang, Yongda; Gao, Joe; Sidhu, Kanwar; Lorenz, Jon C.; et al, Organic Process Research & Development, 2016, 20(1), 95-99

Production Method 2

1360950-40-8

936250-22-5

Reaction Conditions

1.1 Reagents: Hydrochloric acid Solvents: Methanol ,  Dichloromethane ;  rt
1.2 Reagents: Sodium hydroxide Solvents: Water ;  cooled; pH 7, cooled

Reference

Method for synthesizing 2-aminopyrimidine-5-boronic acid

, China, , ,

Production Method 3

1072850-89-5

936250-22-5

Reaction Conditions

1.1 Reagents: Butyllithium ,  Triisopropyl borate Solvents: Tetrahydrofuran ,  Water ;  < -90 °C; -90 °C → -60 °C
1.2 Solvents: Toluene ,  Water ;  -60 °C → rt; 30 min, rt
1.3 Reagents: Hydrochloric acid Solvents: tert-Butyl methyl ether ,  Water ;  4 h, pH 1.3, rt
1.4 Reagents: Sodium hydroxide Solvents: Water ;  1 h, pH 7.5, rt
1.5 Solvents: Isopropanol ,  Water ;  rt → 50 °C; 1 h, 50 °C

Reference

Process for the preparation of boronic acid intermediates

, United States, , ,

Production Method 4

883231-25-2

936250-22-5

Reaction Conditions

1.1 Reagents: Hydrochloric acid Solvents: Water ;  < 30 °C; 12 h, < 30 °C; < 30 °C → 10 °C
1.2 Reagents: Sodium hydroxide Solvents: Water ;  pH 6.5, < 15 °C; 1 h, < 15 °C

Reference

Process for the preparation of (S)-1-[4-[[2-(2-aminopyrimidin-5-yl)-7-methyl-4-morpholinothieno[3,2-d]pyrimidin-6-yl]methyl]piperazin-1-yl]-2-hydroxypropan-1-one (GDC-0980)

, United States, , ,

Production Method 5

7752-82-1

936250-22-5

Reaction Conditions

1.1 Reagents: Butyllithium ,  Triisopropyl borate Solvents: Tetrahydrofuran ,  Hexane ;  1 h, -78 °C; 3.5 h, -78 °C; -78 °C → -20 °C
1.2 Reagents: Water
1.3 Reagents: Hydrogen bromide Solvents: Water ;  pH 6, rt

Reference

New pyrimidylboronic acids and functionalized heteroarylpyrimidines by Suzuki cross-coupling reactions

Clapham, Kate M.; Smith, Amy E.; Batsanov, Andrei S.; McIntyre, Laura; Pountney, Adam; et al, European Journal of Organic Chemistry, 2007, (34), 5712-5716

Production Method 6

209959-33-1

936250-22-5

Reaction Conditions

1.1 Reagents: Butyllithium ,  Triisopropyl borate Solvents: Tetrahydrofuran ;  -80 - -70 °C; 15 min, -80 - -70 °C
1.2 Reagents: Water
1.3 Reagents: Hydrochloric acid Solvents: Methanol ,  Water ;  25 - 30 °C
1.4 Reagents: Sodium hydroxide Solvents: Water ;  pH 7, rt

Reference

Method for synthesis of 2-amino-5-pyrimidineboronic acid pinacol ester

, China, , ,

(2-Aminopyrimidin-5-yl)boronic acid Raw materials

• 5-bromopyrimidin-2-amine
• tert-butyl N-(5-bromopyrimidin-2-yl)-N-[(tert-butoxy)carbonyl]carbamate
• 5-Bromo-2-(2,2,5,5-tetramethyl-1-aza-2,5-disilacyclopent-1-yl)pyrimidine
• (2-((Tert-Butoxycarbonyl)amino)pyrimidin-5-yl)boronic acid
• 2-(N,N-Bis-Boc-amino)pyrimidine-5-boronicacid
• benzhydryliden-(5-bromo-pyrimidin-2-yl)-amine

(2-Aminopyrimidin-5-yl)boronic acid Preparation Products

• (2-Aminopyrimidin-5-yl)boronic acid (936250-22-5)

• 1. Dissolved oxygen sensor based on fluorescence quenching of oxygen-sensitive ruthenium complexes immobilized in sol–gel-derived porous silica coatings
  Analyst, 1996,121, 785-788
• 2. Excimer and exciplex formation in a pair of bright phosphorescent isomers constructed from Cu3(pyrazolate)3 and Cu3I3 coordination luminophores?
  Shun-Ze Zhan,Mian Li,Xiao-Ping Zhou,Dan Li,Seik Weng Ng RSC Adv., 2011,1, 1457-1459
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• 4. Evolutionary de novo design of phenothiazine derivatives for dye-sensitized solar cells?
  Vishwesh Venkatraman,Marco Foscato,Vidar R. Jensen,Bj?rn K?re Alsberg J. Mater. Chem. A, 2015,3, 9851-9860
• 5. Fe3O4/PEG-SO3H as a heterogeneous and magnetically-recyclable nanocatalyst for the oxidation of sulfides to sulfones or sulfoxides
  Saeideh Mirfakhraei,Malak Hekmati,Fereshteh Hosseini Eshbala,Hojat Veisi New J. Chem., 2018,42, 1757-1761

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

• 109299-78-7(5-Pyrimidylboronic acid)
• 696602-91-2(Pyrimidin-5-ylboronic acid hydrate)
• 2241865-88-1((2-aminopyrimidin-5-yl-4,6-d2)boronic acid)
• 2241877-01-8((pyrimidin-5-yl-2-d)boronic acid)
• 2306405-19-4((pyrimidin-5-yl)boronic acid hydrochloride)
• 756817-82-0([2-(dimethylamino)pyrimidin-5-yl]boronic acid)
• 2241865-83-6((pyrimidin-5-yl-d3)boronic acid)
• 1033745-26-4((2-(Methylamino)pyrimidin-5-yl)boronic acid)
• 332062-08-5(Fmoc-S-3-amino-4,4-diphenyl-butyric acid)
• 1270529-38-8(1,2,3,4,5,6-Hexahydro-[2,3]bipyridinyl-6-ol)