m-Chloroperbenzoic acid → HCID 66760404, compound

HRID 1188711Notes

Reaction equation

HRID 1188711 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[CH:5][CH:6]=[C:7]2[C:11]=1[CH:10]([N:12]1[C:17]3[N:18]=[C:19]([S:22][CH3:23])[N:20]=[CH:21][C:16]=3[CH:15]=[CH:14][C:13]1=[O:24])[CH2:9][CH2:8]2.ClC1C=CC=C(C(OO)=[O:33])C=1>ClCCl>[CH3:1][O:2][C:3]1[CH:4]=[CH:5][CH:6]=[C:7]2[C:11]=1[CH:10]([N:12]1[C:17]3[N:18]=[C:19]([S:22]([CH3:23])=[O:33])[N:20]=[CH:21][C:16]=3[CH:15]=[CH:14][C:13]1=[O:24])[CH2:9][CH2:8]2

Participants

4

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 66760455HCID 66760455, compound

Product 1

HCID 66760404HCID 66760404, compoundYield 112.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 8-(7-methoxy-2,3-dihydro-1H-inden-1-yl)-2-(methylthio)pyrido[2,3-d]pyrimidin-7(8H)-one (0.32 g, 0.94 mmol) in dichloromethane (3 mL) was added 3-chloroperbenzoic acid (70%, 0.18 g, 0.73 mmol) and the mixture was stirred at room temperature for 5 h. The reaction mixture was extracted with saturated sodium bicarbonate solution (2×1.5 mL), the organic layer was dried over sodium sulfate, then filtered and evaporated to give 8-(7-methoxy-2,3-dihydro-1H-inden-1-yl)-2-(methylsulfinyl)pyrido[2,3-d]pyrimidin-7(8H)-one as a light brown oil (0.29 g, 0.82 mmol, 87%). ESMS m/z 356 (M+H)+.

Workup

  1. extractionThe reaction mixture was extracted with saturated sodium bicarbonate solution (2×1.5 mL)
  2. dry with materialthe organic layer was dried over sodium sulfate
  3. filtrationfiltered
  4. customevaporated

Sources & evidence

ORD record
ord-287b400772ac4ba8a9dbfba39f43d8af
Source dataset
uspto-grants-2014_03
Patent number
US08674095B2

Reaction notes

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