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

HRID 1107316Notes

Reaction equation

HRID 1107316 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.[CH3:24][NH2:25]>C(Cl)(Cl)Cl>[CH3:24][NH:25][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 6329MethylamineHCID 1355223017-Methylthio-4-oxo-2-(2-propoxyphenyl)-3,4-dihydropyrimido[4,5-d]pyrimidine

Product 1

HCID 1356707567-Methylamino-4-oxo-2-(2-propoxyphenyl)-3,4-dihydropyrimido[4,5-d]pyrimidine

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

7-Methylthio-4-oxo-2-(2-propoxyphenyl)-3,4-dihydropyrimido[4,5-d]pyrimidine (1.40 g) was treated with a solution of methylamine in industrial methylated spirit (33%; 30 ml) in a pressure vessel for 9 hours at 90° C. The reaction mixture was evaporated under reduced pressure to yield a cream solid which was dissolved in chloroform. The organic solution was washed with water, dried (magnesium sulphate) and evaporated under reduced pressure to yield a cream solid. Elution from silica with chloroform:methanol (25:1) yielded a crude product which was recrystallized twice from ethanol to yield the title compound, 0.31 g, m.p. 235-236° C.

Workup

  1. customThe reaction mixture was evaporated under reduced pressure
  2. customto yield a cream solid which
  3. washThe organic solution was washed with water
  4. dry with materialdried (magnesium sulphate)
  5. customevaporated under reduced pressure
  6. customto yield a cream solid
  7. washElution from silica with chloroform:methanol (25:1)
  8. customyielded a crude product which
  9. customwas recrystallized twice from ethanol

Sources & evidence

ORD record
ord-dc2c0e18618c48ce97afd3c19f1fd49d
Source dataset
uspto-grants-2000_05
Patent number
US06060477

Reaction notes

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