Electric Literature of 89088-69-7, A common heterocyclic compound, 89088-69-7, name is 1-Methyl-1H-imidazol-4-amine hydrochloride, molecular formula is C4H8ClN3, its traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc, below Introduce a new synthetic route.
A solution of 1 -methyl- lH-imidazol-4-amine hydrochloride (Intermediate 36 , 16.39 g, 122.74 mmol) and 2,4-dichloro-7-[(4-methylphenyl)sulfonyl]-7H-pyrrolo[2,3-J]pyrimidine (Intermediate 9, 21 g, 61.37 mmol) and DIPEA (42.9 ml, 245.47 mmol) in ethanol (264 ml) were heated at 88 0C overnight. The reaction mixture was cooled to 0 0C and filtered to provide 2-chloro-N-(l -methyl- lEta-imidazol-4-yl)-7-tosyl-7Eta-pyrrolo[2,3-d]pyrimidin-4-amine contaminated with DIPEA. The solid was dissolved in EtOAc (400 ml) and the solution was washed with water (3×100 ml). During the process, the title product crashed out of solution and collected through filtration. Concentration of the mother liquor provided additional title product (total=18.8 g, 76%). LCMS: 403 [M+H]+.1H NMR (300 MHz, DMSO-J6) deltappm 10.75 (br. s., 1 H), 7.96 (d, 2 H), 7.63 (d, 1 H),7.40 – 7.55 (m, 3 H), 7.35 (s, 1 H), 7.23 (br. s., 1 H), 3.68 (s, 3 H), 2.37 (s, 3 H)
The synthetic route of 89088-69-7 has been constantly updated, and we look forward to future research findings.
Reference:
Patent; ASTRAZENECA AB; ASTRAZENECA UK LIMITED; CHUAQUI, Claudio, Edmundo; HUANG, Shan; IOANNIDIS, Stephanos; SHI, Jie; SU, Mei; SU, Qibin; WO2010/38060; (2010); A1;,
Imidazole – Wikipedia,
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