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

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Reaction Conditions

Reaction Steps

To a solution of 6-benzyl-2,4-dichloro-5,6,7,8-tetrahydropyrido[4,3-d]pyrimidine (6.38 g, 21.69 mmol) in anhydrous methanol (100 mL), was added 4.67 N sodium methoxide (5.57 mL, 26 mmol) slowly at 0° C. The reaction mixture was stirred at 0° C. for 15 min, then at rt for 30 min. The reaction mixture was concentrated under reduced pressure. The residue was dissolved in DCM and washed with brine, dried over Na2SO4, filtered, and concentrated to give 6-benzyl-2-chloro-4-methoxy-5,6,7,8-tetrahydropyrido[4,3-d]pyrimidine which was used without the need for purification. 1H NMR (400 MHz, CD2Cl2) δ ppm 7.31-7.40 (m, 4 H), 7.23-7.31 (m, 1 H), 3.95 (s, 3 H), 3.72 (br. s., 2 H), 3.43 (br. s., 2 H), 2.84 (d, J=4.5 Hz, 2 H), 2.78 (d, J=4.0 Hz, 2 H). MS (ESI+) m/z 290.4 (M+H)+.

Provenance & Evidence