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

HRID 127392

Reaction equation

HRID 127392 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

4

Reactant 3

HCID 702EthanolHCID 67105N,N'-DiethylethylenediamineHCID 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 heater 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.

Workup

  1. temperatureat reflux for 3.5 hours
  2. temperatureThen ice-chilling
  3. filtrationthat was filtered off
  4. customre-crystallized from ethanol
  5. customto give 0.9 g

Sources & evidence

ORD record
ord-78fe47c385bf475ea6938a48ab02b1aa
Source dataset
uspto-grants-1981_03
Patent number
US04255568

Linked notes

Loading…