Ethanolamine → 7-(2-Hydroxyethylamino)-4-oxo 2-(2-propoxyphenyl)-3,4-dihydropyrimido[4,5-d]pyrimidine

HRID 1107319Notes

Reaction equation

HRID 1107319 reaction equation
CS[C:3]1[N:8]=[C:7]2[N:9]=[C:10]([C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=3[O:20][CH2:21][CH2:22][CH3:23])[NH:11][C:12](=[O:13])[C:6]2=[CH:5][N:4]=1.[CH2:24]([CH2:26][NH2:27])[OH:25]>C(O)C>[OH:25][CH2:24][CH2:26][NH:27][C:3]1[N:8]=[C:7]2[N:9]=[C:10]([C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=3[O:20][CH2:21][CH2:22][CH3:23])[NH:11][C:12](=[O:13])[C:6]2=[CH:5][N:4]=1

Participants

4

Reactant 2

HCID 700Ethanolamine2×HCID 1355223017-Methylthio-4-oxo-2-(2-propoxyphenyl)-3,4-dihydropyrimido[4,5-d]pyrimidine

Product 1

HCID 1356707847-(2-Hydroxyethylamino)-4-oxo 2-(2-propoxyphenyl)-3,4-dihydropyrimido[4,5-d]pyrimidine

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A stirred mixture of 7-methylthio-4-oxo-2-(2-propoxyphenyl)-3,4-dihydropyrimido[4,5-d]pyrimidine (0.60 g) and ethanolamine (0.25 ml) in ethanol (20 ml) was heated under reflux for 19 hours. More ethanolamine (0.75 ml) was added and stirring under reflux continued for 16 hours. A white crystalline solid which precipitated from the cooled reaction mixture was collected, washed with cold ethanol and recrystallized from ethanol to yield the title compound, 0.38 g, m.p. 204-205.5° C.

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 19 hours
  3. temperatureunder reflux
  4. customA white crystalline solid which precipitated from the cooled reaction mixture
  5. customwas collected
  6. washwashed with cold ethanol
  7. customrecrystallized from ethanol

Sources & evidence

ORD record
ord-4b5410d561a843b48c53f4033055f4fe
Source dataset
uspto-grants-2000_05
Patent number
US06060477

Reaction notes

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