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

HRID 1936652Notes

Reaction equation

HRID 1936652 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-7b3b324904e44215a3485475cb6d2863
Source dataset
uspto-grants-2002_05
Patent number
US06391885B1

Reaction notes

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