Ammonia → 2-(3-Hydroxyphenyl)-9-(2-methoxyphenyl)-9H-purine-6-carboxamide

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Reaction Steps

5-Amino-2-(3-hydroxyphenyl)-6-(2-methoxyphenylamino)pyrimidine-4-carboxamide. A solution of ethyl 5-amino-2-(3-hydroxyphenyl)-6-(2-methoxyphenylamino)pyrimidine-4-carboxylate. (57.8 mg, 0.152 mmol) in anhydrous methanol (5 mL) was chilled to −78° C. The solution was then saturated with ammonia gas. The reaction vessel was sealed at −78° C. and allowed to warm to room temperature. After 18 h the reaction was chilled to −78° C. and opened to atmosphere. The volatiles were evaporated and the resulting material was purified by column chromatography (SiO2, 2% to 5% methanol in methylene chloride) to provide the title compound in 98.3% purity (53 mg, 0.151 mmol, 99% yield). 1H NMR (400 MHz, CD3OD) δ 8.41 (m, 1H), 7.79 (dt, J=8.00, 1.20, 1H), 7.73 (m, 1H), 7.21 (t, J=8.00, 1H), 7.06 (m, 3H), 6.79 (ddd, J=8.00, 2.54, 0.98, 1H), 3.94 (s, 3H); MS (ESI) m/z 352.2 [M+1]+; mp: 230-231° C.

Provenance & Evidence