Methanol → (E)-6-amino-2-cyclopropyl-5-(2-(trimethylsilyl)vinyl)pyrimidine-4-carboxylic acid

Participants

Reaction Steps

(E)-ethyl 6-amino-2-cyclopropyl-5-(2-(trimethylsilyl)vinyl)pyrimidine-4-carboxylate (0.666 g, 2.180 mmol) was dissolved in THF (8.7 mL), MeOH (8.7 mL), and Water (4.4 mL). Lithium hydroxide hydrate (0.274 g, 6.54 mmol) was added as a solid. The reaction mixture was stirred for 15 min at room temperature. The solvent was removed under vacuum. The resulting solid was partitioned between 1 N HCl and ethyl acetate. The aqueous phase was extracted with ethyl acetate three times. The combined organics were washed with saturated sodium chloride, dried over magnesium sulfate, filtered, and concentrated. The solid was triturated with hexane (15 mL) and gently heated with heat gun. The solid from the resulting suspension was collected via filtration and dried under vaccum to provide the title compound as an off-white solid (0.104 g, 17% yield): mp 146-149° C.; 1H NMR (400 MHz, DMSO-d6) δ 0.12 (s, 9H), 0.91-1.03 (m, 4H), 2.02 (tt, J=7.8, 5.1 Hz, 1H), 6.22 (d, J=19.3 Hz, 1H), 6.74 (d, J=19.3 Hz, 1H), 7.34 (s, 2H); ESIMS m/z 278 ([M+H]+), 276 ([M−H]−)

Provenance & Evidence