Methylamine → HCID 69298857, compound

Participants

Reaction Steps

Using general method B, the carbamate of 5-t-butylisoxazol-3-amine (108 mg, 0.480 mmol) and Example A44 (150 mg, 0.480 mmol) were combined to give the intermediate sulfide, 1-(5-tert-butylisoxazol-3-yl)-3-(4-methyl-3-(8-methyl-2-(methylthio)-7-oxo-7,8-dihydropyrido[2,3-d]pyrimidin-6-yl)phenyl)urea (35 mg, 15% yield). Using a procedure analogous to Example A1, 1-(5-tert-butylisoxazol-3-yl)-3-(4-methyl-3-(8-methyl-2-(methylthio)-7-oxo-7,8-dihydropyrido[2,3-d]pyrimidin-6-yl)phenyl)urea (158 mg, 0.330 mmol) and 2.0N solution of methylamine in THF (1.7 mL) were combined and purified by chromatography (Biotage Si-25 column, 60-100% ethyl acetate/Hex) to afford 1-(5-tert-butylisoxazol-3-yl)-3-(4-methyl-3-(8-methyl-2-(methylamino)-7-oxo-7,8-dihydropyrido[2,3-d]pyrimidin-6-yl)phenyl)urea (49 mg, 32% yield). 1H NMR (300 MHz, DMSO-d6): δ 1.26 (s, 9H), 2.06 (s, 3H), 2.90 (s, 3H), 3.53-3.60 (m, 3H), 6.46 (s, 1H), 7.14-7.16 (m, 1H), 7.26-7.28 (m, 1H), 7.32 (s, 1H), 7.67 (s, 1H), 7.65-7.80 (br m, 1H), 8.60-8.65 (m, 1H), 8.72 (s, 1H), 9.47 (s, 1H); MS (ESI) m/z: 462.0 (M+H+).

Provenance & Evidence