Sodium Thiosulfate → 3-(2-chlorophenyl)-7-benzylsulfonyl-3,4-dihydropyrimido[4,5-d]-pyrimidin-2(1H)-one

HRID 478585Notes

Reaction equation

HRID 478585 reaction equation
C(S[C:9]1[N:14]=[C:13]2[NH:15][C:16](=[O:26])[N:17]([C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=3[Cl:25])[CH2:18][C:12]2=[CH:11][N:10]=1)C1C=CC=CC=1.Cl[C:28]1[CH:33]=[CH:32][CH:31]=[C:30]([C:34](OO)=O)[CH:29]=1.[O-:38][S:39]([O-:42])(=S)=O.[Na+].[Na+]>ClCCl>[CH2:34]([S:39]([C:9]1[N:14]=[C:13]2[NH:15][C:16](=[O:26])[N:17]([C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=3[Cl:25])[CH2:18][C:12]2=[CH:11][N:10]=1)(=[O:42])=[O:38])[C:30]1[CH:29]=[CH:28][CH:33]=[CH:32][CH:31]=1

Participants

5

Reactant 3

HCID 24477Sodium ThiosulfateHCID 70297m-Chloroperbenzoic acidHCID 129913387-benzylthio-3-(2-chlorophenyl)-3,4-dihydropyrimido[4,5-d]pyrimidin-2(1H)-one

Product 1

HCID 180024743-(2-chlorophenyl)-7-benzylsulfonyl-3,4-dihydropyrimido[4,5-d]-pyrimidin-2(1H)-one

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A suspension of 1 g (2.61 mmol) of 7-benzylthio-3-(2-chlorophenyl)-3,4-dihydropyrimido[4,5-d]pyrimidin-2(1H)-one in 10 mL of dichloromethane was cooled in ice and treated with 1.29 g (5.23 mmol) of 70% 3-chloroperbenzoic acid. The mixture was stirred at room temperature for 2 hours, then treated with 25 mL of 10% aq. Na2S2O3 and left to stir for 30 minutes. The reaction was diluted with 100 mL dichloromethane and the phases were separated. The organic phase was washed with 10% aq. K2CO3, brine, and then dried over magnesium sulfate and filtered. Concentration of the filtrate under reduced pressure gave 0.73 g of 7-benzylsulfonyl-3-(2-chlorophenyl)-3,4-dihydropyrimido[4,5-d]-pyrimidin-2(1H)-one as a white solid.

Workup

  1. temperaturewas cooled in ice
  2. waitleft
  3. stirringto stir for 30 minutes
  4. customthe phases were separated
  5. washThe organic phase was washed with 10% aq. K2CO3, brine
  6. dry with materialdried over magnesium sulfate
  7. filtrationfiltered

Sources & evidence

ORD record
ord-81b3803338464ea4a56411f4086680c4
Source dataset
uspto-grants-2003_11
Patent number
US06642241B1

Reaction notes

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