m-Chloroperbenzoic acid → 7-(3-Methylsulphinylpropylamino)-4-oxo-2-(2-propoxyphenyl)-3,4-dihydropyrimido[4,5-d]pyrimidine

HRID 1107331Notes

Reaction equation

HRID 1107331 reaction equation
[CH3:1][S:2][CH2:3][CH2:4][CH2:5][NH:6][C:7]1[N:12]=[C:11]2[N:13]=[C:14]([C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=3[O:24][CH2:25][CH2:26][CH3:27])[NH:15][C:16](=[O:17])[C:10]2=[CH:9][N:8]=1.ClC1C=C(C=CC=1)C(OO)=[O:33]>ClCCl>[CH3:1][S:2]([CH2:3][CH2:4][CH2:5][NH:6][C:7]1[N:12]=[C:11]2[N:13]=[C:14]([C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=3[O:24][CH2:25][CH2:26][CH3:27])[NH:15][C:16](=[O:17])[C:10]2=[CH:9][N:8]=1)=[O:33]

Participants

4

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 1356707977-(3-Methylthiopropylamino)-4-oxo-2-(2-propoxyphenyl)-3,4-dihydropyrimido[4,5-d]pyrimidine

Product 1

HCID 1356707617-(3-Methylsulphinylpropylamino)-4-oxo-2-(2-propoxyphenyl)-3,4-dihydropyrimido[4,5-d]pyrimidine

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A cool (0° C.) solution of 7-(3-methylthiopropylamino)-4-oxo-2-(2-propoxyphenyl)-3,4-dihydropyrimido[4,5-d]pyrimidine (1.84 g) and m-chloroperoxybenzoic acid (0.97 g) in dichloromethane (180 ml) was allowed to warm to ambient temperature with stirring. The solution was then stirred for 18 hours at ambient temperature and allowed to stand for 10 days . The reaction mixture was evaporated under reduced pressure and the residue eluted from a silica column with chloroform:methanol (gradient elution). The combined fractions containing product were evaporated under reduced pressure and the residue was recrystallized from isopropanol to yield the title compound, 1.73 g, m. p. 188-9° C.

Workup

  1. stirringThe solution was then stirred for 18 hours at ambient temperature
  2. customThe reaction mixture was evaporated under reduced pressure
  3. washthe residue eluted from a silica column with chloroform
  4. additionThe combined fractions containing product
  5. customwere evaporated under reduced pressure
  6. customthe residue was recrystallized from isopropanol

Sources & evidence

ORD record
ord-a3efbcb493e5447c84f2fbcf7c7d0042
Source dataset
uspto-grants-2000_05
Patent number
US06060477

Reaction notes

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