Methyl 4-methoxy-2-(methylthio)pyrimidine-5-carboxylate → Methyl 4-methoxypyrimidine-5-carboxylate

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Reaction Steps

A mixture of 2.2 g of methyl 4-methoxy-2-(methylthio)pyrimidine-5-carboxylate, 15 g of Raney nickel (washed with methanol to remove water) and 200 mL of methanol was stirred under 1 atm hydrogen overnight. Conversion was incomplete by LCMS so the mixture was filtered and treated with 15 g of fresh Raney nickel under hydrogen overnight. After filtration and concentration under reduced pressure, purification by flash chromatography (0%-10% ethyl acetate in hexanes) gave the product as white crystalline solid: MS (m+1)=169.1; 1H NMR (400 MHz, CDCl3) 9.0 (s, 1H), 8.82 (s, 1H), 4.1 (s, 3H), 3.9 (s, 3H).

Provenance & Evidence