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

HRID 1107332Notes

Reaction equation

HRID 1107332 reaction equation
[CH3:1][S:2]([CH2:4][CH2:5][CH2:6][NH:7][C:8]1[N:13]=[C:12]2[N:14]=[C:15]([C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=3[O:25][CH2:26][CH2:27][CH3:28])[NH:16][C:17](=[O:18])[C:11]2=[CH:10][N:9]=1)=[O:3].ClC1C=C(C=CC=1)C(OO)=[O:34]>ClCCl>[CH3:1][S:2]([CH2:4][CH2:5][CH2:6][NH:7][C:8]1[N:13]=[C:12]2[N:14]=[C:15]([C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=3[O:25][CH2:26][CH2:27][CH3:28])[NH:16][C:17](=[O:18])[C:11]2=[CH:10][N:9]=1)(=[O:34])=[O:3]

Participants

4

Reactant 2

HCID 70297m-Chloroperbenzoic acid2×HCID 1356707617-(3-Methylsulphinylpropylamino)-4-oxo-2-(2-propoxyphenyl)-3,4-dihydropyrimido[4,5-d]pyrimidine

Product 1

HCID 1356707997-(3-Methylsulphonylpropylamino)-4-oxo-2-(2-propoxyphenyl)-3,4-dihydropyrimido[4,5-d]-pyrimidine

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 7-(3-methylsulphinylpropylamino)-4-oxo-2-(2-propoxyphenyl)-3,4,-dihydropyrimido[4,5-d]-pyrimidine (0.80 g) and m-chloroperoxybenzoic acid (0.40 g) in dichloromethane (50 ml) was stirred at ambient temperature for 24 hours. During this time further m-chloroperoxybenzoic acid (about 200 mg) was added on 2 occasions. The solution was washed with dilute aqueous sodium bicarbonate (3×25 ml) and the combined washings back-extracted with a little dichloromethane. The combined organic layer was washed with water and then brine, dried (magnesium sulphate) and evaporated under reduced pressure to yield a residue. This was recrystallized three times from methanol to yield the title compound, 0.51 g, m.p. 222-3° C.

Workup

  1. washThe solution was washed with dilute aqueous sodium bicarbonate (3×25 ml)
  2. extractionthe combined washings back-extracted with a little dichloromethane
  3. washThe combined organic layer was washed with water
  4. dry with materialbrine, dried (magnesium sulphate)
  5. customevaporated under reduced pressure
  6. customto yield a residue
  7. customThis was recrystallized three times from methanol

Sources & evidence

ORD record
ord-bc809a4c262e48baac6648656ba25deb
Source dataset
uspto-grants-2000_05
Patent number
US06060477

Reaction notes

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