m-Chloroperbenzoic acid → HCID 18425509, compound

HRID 1280561Notes

Reaction equation

HRID 1280561 reaction equation
[CH2:1]([S:8][C:9]1[N:14]=[C:13]2[N:15]([CH2:27][CH2:28][N:29]([CH2:32][CH3:33])[CH2:30][CH3:31])[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)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.ClC1C=C(C=CC=1)C(OO)=[O:39]>ClCCl>[CH2:1]([S:8]([C:9]1[N:14]=[C:13]2[N:15]([CH2:27][CH2:28][N:29]([CH2:32][CH3:33])[CH2:30][CH3:31])[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:39])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 18425398HCID 18425398, compound

Product 1

HCID 18425509HCID 18425509, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Oxidation of the 7-benzylthio-3-(2-chlorophenyl)-1-(2-diethylaminoethyl)-3,4-dihydropyrimido[4,5-d]pyrimidin-2(1H)-one was accomplished using 3-chloroperoxybenzoic acid (0.339 g, 1.96 mmol) in dichloromethane with stirring at room temperature for 1 hour. The reaction was quenched with 10% sodium sulfite solution (aq, 5 mL), poured into saturated aqueous sodium bicarbonate, and extracted with dichloromethane. The combined extracts were dried with magnesium sulfate and concentrated in vacuo to provide 7-benzylsulfinyl-3-(2-chlorophenyl)-1-(2-diethylamino-ethyl)-3,4-dihydropyrimido[4,5-d]pyrimidin-2(1H)-one, which was used without purification.

Workup

  1. customThe reaction was quenched with 10% sodium sulfite solution (aq, 5 mL)
  2. additionpoured into saturated aqueous sodium bicarbonate
  3. extractionextracted with dichloromethane
  4. dry with materialThe combined extracts were dried with magnesium sulfate
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-160ac05c9718407a865500db4acc9c5c
Source dataset
uspto-grants-2002_09
Patent number
US06451804B1

Reaction notes

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