Cyclohexanemethanol → HCID 17941787, compound

Participants

Reaction Conditions

Reaction Steps

To a stirred solution of sodium (0.025 g, 1.09 mmol) in cyclohexylmethanol (5 ml, 43 mmol) under nitrogen at 100° C., was added 2-amino-6-benzylamino-4-chloropyrimidine (0.2 g, 0.86 mmol), and the mixture was stirred at 180° C. for 2 h. After removal of solvents, the residue was redissolved in methanol, filtered and the filtrate was evaporated to dryness. The crude product was purified by chromatography on silica, employing petrol: ethyl acetate (8:2) as eluent, to give the title product as a yellow solid (0.13 g, 49%); δH (200 MHz, d6-DMSO) 0.96-1.15 (5H, m, C6H11), 1.23-1.34 (6H, m, C6H11), 4.03 (2H, br s, OCH2), 4.51 (2H, d, C6H5CH2, J=5.31 Hz), 5.12 (1H, s, C(5)H), 6.56 (2H, br s, NH2), 7.20 (1H, br s, NH), 7.28-7.39 (5H, m, C6H5); m/z (+EI) 312 (M+, 100%), 229 (M+-C6H11, 45), 216 (MH+-C6H11CH2, 53), 91 (72).

Provenance & Evidence