Ethanol → N-[2-(diethylamino)ethyl]-7,8-dihydro-5-hydroxy-8-(2-methoxyethyl)-7-oxo-2-phenylpyrido[2,3-d]pyrimidine-6-carboxamide

Reaction equation

C([O:3][C:4]([C:6]1[C:21](=[O:22])[N:20]([CH2:23][CH2:24][O:25][CH3:26])[C:9]2[N:10]=[C:11]([C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=3)[N:12]=[CH:13][C:8]=2[C:7]=1[OH:27])=O)C.C([NH:30][CH2:31][CH2:32][NH:33][CH2:34][CH3:35])C.[CH2:36](O)[CH3:37]>>[CH2:36]([N:33]([CH2:34][CH3:35])[CH2:32][CH2:31][NH:30][C:4]([C:6]1[C:21](=[O:22])[N:20]([CH2:23][CH2:24][O:25][CH3:26])[C:9]2[N:10]=[C:11]([C:14]3[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=3)[N:12]=[CH:13][C:8]=2[C:7]=1[OH:27])=[O:3])[CH3:37]

Participants

Reactant 3

HCID 702Ethanol

HCID 67105N,N'-Diethylethylenediamine

HCID 54727901Ethyl 5-hydroxy-8-(2-methoxyethyl)-7-oxo-2-phenyl-7,8-dihydropyrido[2,3-d]pyrimidine-6-carboxylate

Product 1

HCID 54724568N-[2-(diethylamino)ethyl]-7,8-dihydro-5-hydroxy-8-(2-methoxyethyl)-7-oxo-2-phenylpyrido[2,3-d]pyrimidine-6-carboxamide

Procedure

To 1.0 g. (0.0027 mole) of 7,8-dihydro-5-hydroxy-8-(2-methoxyethyl)-7-oxo-2-phenylpyrido[2,3-d]pyrimidine-6-carboxylic acid ethyl ester (prepared as in Example 9) was added to 0.63 g. (0.0054 mole) of diethylethylenediamine in 25 ml. of ethanol. This mixture was heated at reflux for 3.5 hours. Then ice-chilling caused the formation of a white solid that was filtered off and re-crystallized from ethanol to give 0.9 g. of product with a m.p. 115°-117° C.