m-Chloroperbenzoic acid → HCID 18425464, compound

HRID 1280564Notes

Reaction equation

HRID 1280564 reaction equation
[CH2:1]([S:8][C:9]1[N:14]=[C:13]2[N:15]([CH:27]([CH2:32][O:33][CH2:34][CH3:35])[CH2:28][O:29][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=CC=C(C(OO)=[O:44])C=1>ClCCl>[CH2:1]([S:8]([C:9]1[N:14]=[C:13]2[N:15]([CH:27]([CH2:32][O:33][CH2:34][CH3:35])[CH2:28][O:29][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:44])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 18425418HCID 18425418, compound

Product 1

HCID 18425464HCID 18425464, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A suspension of 7-benzylthio-3-(2-chlorophenyl)-1-(2-ethoxy-1-ethoxymethylethyl)-3,4-dihydropyrimido[4,5-d]pyrimidin-2(1H)-one (566 mg, 1.1 mmol) in dichloromethane (5 mL) was cooled in an ice bath and 3-chloroperbenzoic acid was added. The reaction mixture was stirred for 1 hour, concentrated in vacuo, and the residue was purified by column chromatography on silica gel using 98:2 dichloromethane/methanol. The column fractions containing product were combined and concentrated in vacuo to yield 425 mg of 7-benzylsulfinyl-3-(2-chlorophenyl)-1-(2-ethoxy-1-ethoxymethylethyl)-3,4-dihydropyrimido[4,5-d]pyrimidin-2(1H)-one.

Workup

  1. temperaturewas cooled in an ice bath
  2. concentrationconcentrated in vacuo
  3. customthe residue was purified by column chromatography on silica gel using 98:2 dichloromethane/methanol
  4. additionThe column fractions containing product
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-4bcc240296904f23a4d1e947bbf176f8
Source dataset
uspto-grants-2002_09
Patent number
US06451804B1

Reaction notes

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