2-Chloro-4,6-dimethoxy-1,3,5-triazine → 2-Bromo-N-methoxy-N-methylisonicotinamide

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Reaction Steps

2-Bromo-isonicotinic acid (0.5 g, 2.47 mmol) was dissolved in dry THF (10 mL). 2-Chloro-4,6-dimethoxy[1,3,5]triazine (0.77 g, 4.4 mmol) and diisopropylethylamine (0.96 g, 0.74 mmol) were added and the solution was stirred for 1 hour after which N,O-dimethyl hydroxylamine hydrochloride (0.241 g, 2.47 mmol) was added. The mixture was stirred for a further 16 hours at room temperature and then diluted with water (15 mL). The aqueous mixture was then extracted with EtOAc (3×10 mL). The combined organics were washed successively with a saturated aqueous Na2CO3, 1N aqueous HCl and then brine. The organic phase was dried (Na2SO4) and then evaporated to dryness. Purification by SiO2 chromatography (eluting with EtOAc/hexane; 2:1) gave a product which was then suspended in Et2O. The insoluble material was removed by filtration and the filtrate was evaporated in vacuo to give 2-bromo-N-methoxy-N-methyl-isonicotinamide (0.342 g, 56%). MS(ESI) m/z 244.9 (M+H)+

Provenance & Evidence