m-Chloroperbenzoic acid → 8-(2-cyclopropylbenzyl)-2-(methylsulfinyl)pyrido[2,3-d]pyrimidin-7(8H)-one

HRID 1188717Notes

Reaction equation

HRID 1188717 reaction equation
[CH:1]1([C:4]2[CH:23]=[CH:22][CH:21]=[CH:20][C:5]=2[CH2:6][N:7]2[C:12]3[N:13]=[C:14]([S:17][CH3:18])[N:15]=[CH:16][C:11]=3[CH:10]=[CH:9][C:8]2=[O:19])[CH2:3][CH2:2]1.ClC1C=CC=C(C(OO)=[O:32])C=1>ClCCl>[CH:1]1([C:4]2[CH:23]=[CH:22][CH:21]=[CH:20][C:5]=2[CH2:6][N:7]2[C:12]3[N:13]=[C:14]([S:17]([CH3:18])=[O:32])[N:15]=[CH:16][C:11]=3[CH:10]=[CH:9][C:8]2=[O:19])[CH2:3][CH2:2]1

Participants

4

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 667608898-(2-cyclopropylbenzyl)-2-(methylthio)pyrido[2,3-d]pyrimidin-7(8H)-one

Product 1

HCID 667606708-(2-cyclopropylbenzyl)-2-(methylsulfinyl)pyrido[2,3-d]pyrimidin-7(8H)-oneYield 85.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of 8-(2-cyclopropylbenzyl)-2-(methylthio)pyrido[2,3-d]pyrimidin-7(8H)-one (88 mg, 0.27 mmol) in dichloromethane (1 mL) was added 3-chloroperbenzoic acid (70%, 67 mg, 0.27 mmol) at 0-5° C. and the mixture was stirred at room temperature for 18 h. After completion, it was diluted with dichloromethane (10 mL) and washed with saturated sodium bicarbonate solution (1×5 mL) then with water (1×5 mL). The organic layer was dried over sodium sulfate, filtered and evaporated to give 8-(2-cyclopropylbenzyl)-2-(methylsulfinyl)pyrido[2,3-d]pyrimidin-7(8H)-one as a pale yellow solid (80 mg, 0.23 mmol, 85%). ESMS m/z 340 (M+H)+.

Workup

  1. washwashed with saturated sodium bicarbonate solution (1×5 mL)
  2. dry with materialThe organic layer was dried over sodium sulfate
  3. filtrationfiltered
  4. customevaporated

Sources & evidence

ORD record
ord-4250513bd14f4bfa86251bd8d603e5ff
Source dataset
uspto-grants-2014_03
Patent number
US08674095B2

Reaction notes

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