Sodium hydride → tert-butyl 2-methoxyethyl((4-oxo-4,5,7,8-tetrahydro-3H-pyrano[4,3-d]pyrimidin-2-yl)methyl)carbamate

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Reaction Steps

To a solution of tert-butyl 2-methoxyethylcarbamate (185 mg, 1.06 mmol) in anhydrous tetrahydrofuran (5 mL) was added sodium hydride (95%, 127 mg, 4.28 mmol) portion-wise slowly, followed by 2-(chloromethyl)-7,8-dihydro-3H-pyrano[4,3-d]pyrimidin-4(5H)-one (212 mg, 1.6 mmol). The reaction mixture was stirred for 48 h. The reaction was quenched with water (approximately 3 mL) and the solvent evaporated. The residue was re-dissolved in acetonitrile and purified by column chromatography (100% dichloromethane for 5 min, then slow gradient up to 15% methanol in dichloromethane). The resulting clear oil was dissolved with 0.5 mL of acetonitrile and heated in vacuo to give the title compound as a white solid (179 mg). 1H NMR (400 MHz, chloroform-d) 8 ppm 4.60 (s, 2H) 4.21-4.34 (m, 2H) 3.91-4.01 (m, 3H) 3.66-3.79 (m, 2H) 3.51-3.66 (m, 6H) 2.71-2.80 (m, 2H) 1.48 (s, 3H) 1.35 (s, 6H). MS (m/z, MH+): 340.4

Provenance & Evidence