Sodium Chloride → 4-(5-Methyl-3-phenylisoxazol-4-yl)pyrimidin-2-amine

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Reaction Steps

The above Compound 3 (17.7 g, 0.088 mol) and dimethylformamide dimethyl acetal (DMF.DMA) (160 g, 0.132 mol) were refluxed overnight. To the reaction mixture was added ethyl acetate and saturated aqueous NaCl. The organic phase was washed with saturated aqueous NaCl (twice) and dried (MgSO4). The organic solvent was removed under reduced pressure, and the crude product material was dissolved in 200 mL methanol. To the solution was added guanidine hydrochloride (10.5 g, 0.110 mol) in 100 mL methanol, followed by sodium methoxide (6.17 g, 0.114 mol) in 100 mL methanol. The reaction mixture was refluxed overnight and then was cooled to room temperature. The reaction solvent was concentrated to approximately 100 mL total volume, and the precipitated product was filtered. The filtration cake afforded the title compound (9.3 g). The overall yield for two steps was 46%.

Provenance & Evidence