Sodium hydride → HCID 58739083, compound

Participants

Reaction Steps

Reaction of 2-methanesulfonyl-5-benzyloxy-1-methyl-6-oxo-1,6-dihydro-pyrimidine-4-carboxylic acid ethyl ester (2.21 g, 6.03 mmol) and [1,2]thiazinane 1,1-dioxide (0.97 g, 7.2 mmol) in dry N,N-dimethylformamide (30 ml) with sodium hydride (0.35 g of a 60% dispersion in mineral oil, 8.8 mmol) gave 2.35 g (92% yield) of the title ester as white needles; mp 109–110° C. 1HNMR 400 MHz (CDCl3) δ (ppm): 1.29 (3H, t, J=7.1 Hz, CH3), 1.62 (1H, m, CH), 2.3–2.6 (3H, m, CH2 and CH), 3.15–3.21 (1H, m, CH), 3.5–3.6 (1H, m, CH), 3.64 (3H, s, NCH3), 3.64 (1H, m overlapping with NCH3, CH), 3.97–4.05 (1H, m, CH), 4.32 (2H, q, J=7.1 Hz, OCH2), 5.29 (2H, AB system, JAB=10.6 Hz, Δν=62.5 Hz, OCH2), 7.3–7.5 (5H, m, aromatics). Anal. Calcd for C19H23N3O6S: C 54.15, H 5.50, N 9.97. Found: C 53.88, H 5.40, N 9.91.

Provenance & Evidence