Benzene → HCID 136082964, compound

Participants

Reaction Steps

3-(2-Acetylamino-4-diacetylamino-1,6-dihydro-6-oxo-5-pyrimidinyl)propionaldehyde diethyl acetal (25.0 g, 0.66 mol) was heated with 100 ml of water on a steam bath for 4 hours. The solution was filtered hot to remove an insoluble by-product, and the filtrates were spin evaporated in vacuo to a thick syrup. This syrup was successively dissolved in ethanol and then ethylacetate followed by spin evaporation each time to give a solid which was digested with ethyl acetate. The solids were collected and dried; yield, 15.1 g (76%), mp 199°-201° of a cream colored solid which was used without further purification. Recrystallization of a portion from 2-propanol gave the analytical sample, mp 202°-205°; TLC (C6H6 :EtOH/10:1): NMR (DMSO-d6) δ11.75 (br s, 1H, NH), 11.30 (br s, 1H, NH, W1/2=5 Hz), 6.15 (d, 1H, J=5.0 Hz, OH), 6.06 (m, 1H, J= 2.7 Hz when D2O exchange removed OH CH), 2.43 (s, 3H, CH3), 2.17 (s, 3H, CH3), 2.40-2.10 (m, 2H, pyrimidine-CH2), 2.02-1.42 (m, 2H, CH2CH2CH); 13C-FT nmr (DMSO-d6) ppm: 15.7, 23.9, 27.2, 72.8, 102.2, 147.2, 152.4, 160.4, 171.0, 173.4; MS m/e 266, 248.

Provenance & Evidence