Sodium Hydroxide → 5-Benzyloxy-1-methyl-6-oxo-2-p-tolylmethanesulfonyl-amino-1,6-dihydro-pyrimidine-4-carboxylic acid methylamide

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Reaction Steps

Potassium tert-butoxide (93.8 mg, 836 μmol) was added to a solution of 2-amino-5-(benzyloxy)-N,1-dimethyl-6-oxo-1,6-dihydropyrimidine-4-carboxamide (110 mg, 380 μmol) in THF (10 ml) in DMF (2 ml) [Comment: please check]. After 10 min., the reaction mixture was cooled by an ice bath and then a solution of (4-methylphenyl)methanesulfonyl chloride (93.7 mg, 458 μmol) in THF (2 ml) was added. After 70 min., EtOAc and 1 N NaOH aqueous solution were added. The organic phase was extracted with EtOAc and then with DCM. The combined organic phases were washed with water, and brine, dried over Na2SO4 and evaporated to dryness. Chromatography (silica gel, 0 to 2% MeOH in DCM) provided the title compound as a pale yellow solid (0.080 g; 46%). LCMS: m/z=457 (MH+).

Provenance & Evidence