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

HRID 2058386Notes

Reaction equation

HRID 2058386 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 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.

Workup

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

Sources & evidence

ORD record
ord-498f55b03e254a9ba1734109badc393e
Source dataset
uspto-grants-1980_07
Patent number
US04215216

Reaction notes

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