Diethyl Oxalate → Ethyl 6-(benzyloxy)-1-(2-methoxyethyl)-5-oxo-1,2,3,5-tetrahydroimidazo[1,2-a]pyrimidine-7-carboxylate

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Reaction Steps

Reaction of the adduct of diethyl oxalate (16.95 g, 0.116 mol), ethyl benzyloxyacetate (22.53 g, 0.116 mol) and sodium hydride (5.10 g of a 60% dispersion in mineral oil, 0.127 mol) with 1-(2-methoxyethyl)-4,5-dihydro-1H-imidazol-2-amine hydrobromide (26.0 g, 0.116 mol) as described for intermediate 1 gave 5.37 g (12% yield) of the title ester as a clear oil. 1HNMR 400 MHz (CDCl3) δ (ppm): 1.31 (3H, t, J=7.1 Hz, CH3), 3.38 (3H, s, OCH3), 3.61 (4H, s, 2×CH2), 3.84 (2H, t, J=8.9 Hz, CH2), 4.14 (2H, t, J=8.9 Hz, CH2), 4.32 (2H, q, J=7.1 Hz, OCH2), 5.09 (2H, s, OCH2), 7.3-7.38 (3H, m, aromatics), 7.49 (2H, m, aromatics). MS (ESI+) m/e 374 [M+H+].

Provenance & Evidence