Di-tert-butyl diazene-1,2-dicarboxylate → 1,2-Hydrazinedicarboxylic acid, 1-[4-methoxy-2-(methylthio)-5-pyrimidinyl]-, 1,2-bis(1,1-dimethylethyl) ester

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Reaction Steps

To a solution of 5-bromo-4-methoxy-2-(methylthio)pyrimidine (25.3 g, 108 mmol) in THF (250 mL) was added under argon isopropylmagnesium chloride LiCl in THF (108 mL, 140 mmol) at 0° C. The mixture was allowed to warm up to rt and stirred for 1 h. di-tert-butylazodicarboxylate (24.8 g, 108 mmol) was added and the mixture was stirred 1 h at rt, quenched by addition of a saturated aqueous solution of ammonium chloride (250 mL) then extracted with EtOAc. The organic layer was washed with a saturated aqueous solution of ammonium chloride, dried (Na2SO4), filtered and concentrated. The crude material was purified by silica gel column chromatography (hexane/EtOAc, 100:0→75:25) to afford 37.2 g of the title compound as a white solid. tR: 1.17 min (LC-MS 4); ESI-MS: 387.3 [M+H]+ (LC-MS 4), Rf=0.79 (hexane/EtOAc, 1:1).

Provenance & Evidence