Cyclopentylamine → 4-(Cyclopentylamino)-2-(methylthio)pyrimidine-5-carbaldehyde

Participants

Reaction Steps

Ethyl 4-chloro-2-(methylthio)pyrimidine-5-carboxylate (17 g, 73 mmol) and cyclopentylamine (12.4 g, 146 mmol) were combined by the 3-step procedure of Example C1 to provide 4-cyclopentylamino-2-methylsulfanyl-pyrimidine-5-carbaldehyde (8.5 g, 49% yield over 3 steps). 1H NMR (400 MHz, DMSO-d6): δ 9.73 (s, 1 H), 8.55 (d, J=6.4 Hz, 1 H), 8.51 (s, 1 H), 4.43 (m, 1 H), 2.50 (s, 3 H, obscured by DMSO), 2.03-1.98 (m, 2 H), 1.69-1.48 (m, 6 H); MS (ESI) m/z: 238.3 [M+H]+.

Provenance & Evidence