Production Method 1

3934-20-1

920-39-8

941294-36-6

Reaction Conditions

1.1 Catalysts: Iron(II) acetylacetonate Solvents: Tetrahydrofuran ;  -78 °C; 20 min, -78 °C
1.2 Solvents: Water ;  -78 °C

Reference

Efficient Discovery of Potent Anti-HIV Agents Targeting the Tyr181Cys Variant of HIV Reverse Transcriptase

Jorgensen, William L.; Bollini, Mariela; Thakur, Vinay V.; Domaoal, Robert A.; Spasov, Krasimir A.; et al, Journal of the American Chemical Society, 2011, 133(39), 15686-15696

Production Method 2

79-31-2

1722-12-9

941294-36-6

Reaction Conditions

1.1 Reagents: Ammonium persulfate ,  Silver nitrate Solvents: Dichloromethane ,  Water ;  rt; 16 h, 25 °C

Reference

Preparation of triazole-pyridinyl-substituted azacyclohexyl acetic acid compounds as LPA receptor antagonists for the treatment and prevention of diseases

, World Intellectual Property Organization, , ,

Production Method 3

79-31-2

1722-12-9

941294-36-6

Reaction Conditions

1.1 Reagents: Potassium persulfate Catalysts: Silver nitrate Solvents: Dichloromethane ,  Water ;  12 h, rt

Reference

Silver catalysed decarboxylative alkylation and acylation of pyrimidines in aqueous media

Mai, Wen-Peng; Sun, Bin; You, Li-Qin; Yang, Liang-Ru; Mao, Pu; et al, Organic & Biomolecular Chemistry, 2015, 13(9), 2750-2755

Production Method 4

72-18-4

1722-12-9

941294-36-6

Reaction Conditions

1.1 Reagents: Trifluoroacetic acid ,  Ammonium persulfate Solvents: 1,2-Dichloroethane ,  Water ;  1 min, rt
1.2 Catalysts: Silver nitrate Solvents: Water ;  rt → 80 °C; 24 h, 80 °C

Reference

Unprotected Amino Acids as Stable Radical Precursors for Heterocycle C-H Functionalization

Mai, Duy N.; Baxter, Ryan D., Organic Letters, 2016, 18(15), 3738-3741

2-Chloro-4-isopropylpyrimidine Raw materials

• L-Valine
• 2,4-Dichloropyrimidine
• 2-Methylpropanoic acid
• 2-Chloropyrimidine
• Isopropylmagnesium Bromide Solution (2.9 M in 2-methyltetrahydrofuran)

2-Chloro-4-isopropylpyrimidine Preparation Products

• 2-Chloro-4-isopropylpyrimidine (941294-36-6)

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Professional Introduction to 2-Chloro-4-isopropylpyrimidine (CAS No. 941294-36-6)

2-Chloro-4-isopropylpyrimidine, with the chemical formula C?H?ClN? and CAS number 941294-36-6, is a significant compound in the field of pharmaceutical and agrochemical research. This heterocyclic organic compound features a pyrimidine core, which is a crucial structural motif in many biologically active molecules. The presence of both chloro and isopropyl substituents on the pyrimidine ring imparts unique reactivity and functional properties, making it a valuable intermediate in synthetic chemistry.

The compound's structure is characterized by a six-membered aromatic ring containing two nitrogen atoms. The 2-chloro substituent at the 2-position enhances its electrophilicity, facilitating nucleophilic substitution reactions, while the 4-isopropyl group at the 4-position provides steric hindrance and influences electronic distribution across the ring. These features make 2-Chloro-4-isopropylpyrimidine a versatile building block for constructing more complex molecules.

In recent years, 2-Chloro-4-isopropylpyrimidine has garnered attention in the development of novel pharmaceutical agents. Its pyrimidine scaffold is closely related to many known bioactive compounds, including antiviral, anticancer, and antimicrobial agents. The chloro group allows for further functionalization via cross-coupling reactions such as Suzuki-Miyaura or Buchwald-Hartwig couplings, enabling the introduction of aryl or amino groups, respectively.

One of the most promising applications of 2-Chloro-4-isopropylpyrimidine is in the synthesis of kinase inhibitors. Kinases are enzymes that play a critical role in cell signaling pathways and are frequently targeted in drug development due to their involvement in various diseases, including cancer. Researchers have utilized this compound as a key intermediate to develop potent inhibitors with improved selectivity and reduced toxicity. For instance, derivatives of 2-Chloro-4-isopropylpyrimidine have been explored as inhibitors of tyrosine kinases, showing promise in preclinical studies.

The agrochemical industry has also benefited from the utility of 2-Chloro-4-isopropylpyrimidine. Its structural motifs are found in several herbicides and fungicides that target specific enzymes or metabolic pathways in plants. By modifying the substituents on the pyrimidine ring, chemists can fine-tune the biological activity of these compounds, leading to more effective crop protection agents. Recent studies have highlighted its role in developing next-generation pesticides with enhanced environmental compatibility.

The synthesis of 2-Chloro-4-isopropylpyrimidine typically involves multi-step organic reactions starting from readily available precursors. A common synthetic route includes chlorination of an appropriately substituted pyrimidine derivative followed by isopropylation. Advances in catalytic systems have enabled more efficient and sustainable production methods, reducing waste and improving yields. These improvements align with global efforts to promote green chemistry principles.

In terms of analytical characterization, modern techniques such as nuclear magnetic resonance (NMR) spectroscopy, mass spectrometry (MS), and high-performance liquid chromatography (HPLC) are employed to confirm the structure and purity of 2-Chloro-4-isopropylpyrimidine. These methods provide detailed insights into its molecular architecture and help ensure consistency across different batches.

The pharmacological potential of this compound extends beyond kinase inhibition. Emerging research suggests that derivatives of 2-Chloro-4-isopropylpyrimidine may exhibit antiviral properties by interfering with viral replication cycles. The pyrimidine core is structurally analogous to nucleobases found in DNA and RNA, suggesting that these compounds could disrupt viral genetic material synthesis or integration into host cells. Preliminary computational studies have identified promising candidates for further experimental validation.

The industrial production and handling of 2-Chloro-4-isopropylpyrimidine must adhere to stringent safety protocols due to its reactivity and potential health hazards. Proper ventilation, personal protective equipment (PPE), and waste disposal procedures are essential to mitigate risks associated with its use in laboratories and manufacturing facilities. Regulatory agencies continue to monitor advancements in chemical safety to ensure best practices are followed.

The future prospects for 2-Chloro-4-isopropylpyrimidine are bright, with ongoing research exploring new applications and synthetic methodologies. Collaborative efforts between academia and industry are driving innovation in drug discovery and agrochemical development. As our understanding of molecular interactions deepens, compounds like 2-Chloro-4-isopropylpyrimidine will remain indispensable tools for creating novel solutions to global challenges.

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