4-Chloro-1-methyl-1H-pyrazolo[3,4-d]pyrimidine

Uses

4-Chloro-1-methyl-1H-pyrazolo[3,4-d]pyrimidine is a chlorine-substituted organic compound. It is a crucial compound that could be used as a pharmaceutical intermediate in pharmaceutical synthesis and scientific research.

Synthesis

General procedure for the synthesis of 1-methyl-4-chloropyrazolo[3,4-d]pyrimidines from 4-chloro-1H-pyrazolo[3,4-d]pyrimidines (1.88 g, 0.012 mol) and iodomethane (2.56 g, 0.018 mol): 4-chloro-1H-pyrazolo[3,4-d]pyrimidines and NaH (0.864 g, 0.036 mol) suspension in anhydrous DMF (10 mL) was stirred for 30 min. Subsequently, iodomethane was added and the reaction mixture was stirred overnight at room temperature. Upon completion of the reaction, the reaction was quenched with 100 mL of water and extracted with EtOAc (60 mL x 3). The organic layers were combined and concentrated under reduced pressure to afford the target product 1-methyl-4-chloropyrazolo[3,4-d]pyrimidine. Yield: 70.8%; 1H-NMR (400 MHz, DMSO-d6) δ 8.85 (s, 1H), 8.44 (s, 1H), 4.08 (s, 3H).

References

[1] Comptes Rendus Chimie, 2017, vol. 20, # 9-10, p. 927 - 933
[2] Molecules, 2017, vol. 22, # 4,
[3] Patent: CN107383014, 2017, A. Location in patent: Paragraph 0079; 0080; 0081; 0082
[4] European Journal of Medicinal Chemistry, 2018, vol. 155, p. 210 - 228