Methyl formate → Methyl 3-(4-oxo-2-thioxo-1,2,3,4-tetrahydro-5-pyrimidinyl)propanoate

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Reaction Steps

To a suspension of potassium tert-butoxide (7.29 g, 64.9 mmol) in t-butylmethyl ether (100 mL) was added a solution of dimethyl pentanedioate (5.2 g, 32.5 mmol) and methyl formate (1.950 g, 32.5 mmol) in t-butylmethyl ether (50 mL). The mixture was stirred overnight and concentrated to dryness afford the yellow oil. The oil was dissolved in methanol (80 mL), to which thiourea (2.72 g, 35.7 mmol) was added. The mixture was heated to reflux overnight. The result mixture was concentrated and dissolved in water, adjust pH to 3 with AcOH. The solution was extracted with DCM three times. The combined organic layers were dried over Na2SO4, filtered and concentrated to afford the title compound (2.1 g, 9.80 mmol, 30.2% yield).

Provenance & Evidence