Hydrochloric Acid → 4-Amino-2-(methylsulfanyl)pyrimidine-5-carbaldehyde

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To a solution of 4-amino-2-(methylthio)pyrimidine-5-carbonitrile (3.0 g, 18.05 mmol) in THF (100 mL) is added diisobutylaluminum hydride (41.52 mL, 1.0 M in CH2Cl2, 41.52 mmol) at 0° C. After the mixture is stirred for 2.5 hours at 0° C., hydrochloric acid (2N, 30 mL) is added and stirring is continued for 20 minutes. To the reaction mixture is added saturated Na2CO3 until a pH of 8 is achieved. The suspended material is filtered through Celit pad and washed with K2CO3 solution. The solution is diluted with EtOAc and washed with saturated K2CO3, brine and dried, filtered and concentrated to give crude product, which is purified by flash silica gel column, eluting with hexane (100%) gradient to hexane/ether (60/40%), to give the title intermediate as a solid (1.62 g, 53.1%).

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