Methanol → 8-(2-bromobenzyl)-2-(methylsulfonyl)pyrido[2,3-d]pyrimidin-7(8H)-one

HRID 1188714Notes

Reaction equation

HRID 1188714 reaction equation
[Br:1][C:2]1[CH:21]=[CH:20][CH:19]=[CH:18][C:3]=1[CH2:4][N:5]1[C:10]2[N:11]=[C:12](SC)[N:13]=[CH:14][C:9]=2[CH:8]=[CH:7][C:6]1=[O:17].O[O:23][S:24]([O-:26])=O.[K+].[CH3:28]O>O>[Br:1][C:2]1[CH:21]=[CH:20][CH:19]=[CH:18][C:3]=1[CH2:4][N:5]1[C:10]2[N:11]=[C:12]([S:24]([CH3:28])(=[O:26])=[O:23])[N:13]=[CH:14][C:9]=2[CH:8]=[CH:7][C:6]1=[O:17]

Participants

5

Reactant 3

HCID 887MethanolHCID 23707502Potassium hydroxy sulfiteHCID 667614708-(2-bromobenzyl)-2-(methylthio)pyrido[2,3-d]pyrimidin-7(8H)-one

Product 1

HCID 667603438-(2-bromobenzyl)-2-(methylsulfonyl)pyrido[2,3-d]pyrimidin-7(8H)-oneYield 65%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a solution of 8-(2-bromobenzyl)-2-(methylthio)pyrido[2,3-d]pyrimidin-7(8H)-one (0.24 g, 0.66 mmol) in methanol (20 mL) was added the solution of Oxone (720 mg, 1.17 mmol) in water (10 mL). The mixture was stirred for 18 h, then evaporated to dryness. The residue was dissolved in the mixture of dichloromethane (20 mL) and water (20 mL), separated, and the aqueous layer was extracted with dichloromethane (1×20 mL), and the combined organic layers were dried over sodium sulfate, filtered and concentrated in vacuo to give 8-(2-bromobenzyl)-2-(methylsulfonyl)pyrido[2,3-d]pyrimidin-7(8H)-one as a beige solid (0.17 g, 0.43 mmol, 65%). ESMS m/z 394 (M+H)+.

Workup

  1. customevaporated to dryness
  2. dissolutionThe residue was dissolved in the mixture of dichloromethane (20 mL) and water (20 mL)
  3. customseparated
  4. extractionthe aqueous layer was extracted with dichloromethane (1×20 mL)
  5. dry with materialthe combined organic layers were dried over sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-57e6054b2d9e4a41b9db7312c7f1dab1
Source dataset
uspto-grants-2014_03
Patent number
US08674095B2

Reaction notes

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