Methylamine → HCID 18442526, compound

Participants

Reaction Conditions

Reaction Steps

A solution of ethyl intermediate 9, 5-benzyloxy-1-(2-methoxycarbonylethyl)-2-methylsulfonyl-6-oxo-1,6-dihydro-pyrimidine-4-carboxylate, (0.594 g, 1.35 mmol) in tetrahydrofuran (10 ml) was treated with 10 ml (20 mmol) of a 2M solution of methylamine in tetrahydrofuran and the resulting mixture stirred at 22° C. for 1 h. The solvent was then evaporated in vacuo and the residue diluted with toluene and heated under reflux for 2.5 h. The reaction mixture was then diluted with ethyl acetate washed successively with saturated sodium bicarbonate and brine then dried over anhydrous magnesium sulfate. Evaporation of the solvent followed by chromatography on silica gel (elution gradient of ethyl acetate 0–20% in toluene) gave 0.374 g (77% yield) of the title ester as white crystals; mp 121° C. (ethyl acetate/hexane). 1HNMR 400 MHz (CDCl3) δ (ppm): 1.31 (3H, t, J=7.1 Hz, CH3), 2.82 (2H, t, J=7.0 Hz, CH2), 3.42 (3H, s, NCH3), 4.27 (2H, t, J=7.0 Hz, CH2), 4.33 (2H, q, J=7.1 Hz, OCH2), 5.20 (2H, s, OCH2), 7.36 (3H, m, aromatics), 7.47 (2H, m, aromatics). Anal. Calcd for C18H19N3O5: C, 60.49; H, 5.35; N, 11.75. Found: C, 60.12; H, 5.04; N, 11.49.

Provenance & Evidence