Sodium Methoxide → 3-Pyridinamine, 4-chloro-2-methoxy-

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Reaction Steps

To a stirred solution of 2-bromo-4-chloropyridin-3-amine (prepared as described in US2002/0119982) (1.0 eq.) in dry MeOH (0.25M) under argon was added a solution of NaOMe (25% wt in MeOH, 1.5 eq.) and the reaction mixture was refluxed for 1 h, more NaOMe (25% wt in MeOH, 1.5 eq) was added and the reaction mixture was refluxed for an additional 2 h. The volatiles were removed under reduced pressure and the crude product was purified by flash chromatography eluting with 2-10% EtOAc/petroleum ether affording the titled compound as yellow oil. 1H-NMR (300 MHz, DMSO-d6, 300K) δ 7.33 (1H, d, J=5.5 Hz), 6.88 (1H, d, J=5.5 Hz), 5.13 (2H, bs), 3.89 (3H, s). MS (ES) C6H7ClN2O requires: 158, found: 159, 161 (M+H)+.

Provenance & Evidence