2-Chloropyrimidine → 6-Benzyl-4-methoxy-5,6,7,8-tetrahydropyrido[4,3-d]pyrimidine

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Reaction Steps

A 1 L flask was charged with 6-benzyl-4-chloro-5,6,7,8-tetrahydropyrido[4,3-d]pyrimidine (39.6 g, 0.152 mol) and methanol (300 mL), and the mixture was heated to dissolve the chloropyrimidine. 4.37 M of sodium methoxide in methanol (105 mL) was added slowly to the warm mixture and the stirred mixture rapidly turned cloudy. The resultant suspension was heated under reflux for 2 h. After cooling, the mixture was concentrated in vacuo to ca 100 mL. The residue was poured into water (600 mL), and extracted with CH2Cl2 (200 mL×2). The combined organic layers were washed with brine (400 mL), dried (Na2SO4), filtered and concentrated in vacuo to a light brown oil (38.9 g, 100%). MS: 256.1 [M+1]+.

Provenance & Evidence