m-Chloroperbenzoic acid → 6-Bromo-8-ethyl-2-methylsulfinylpyrido[2,3-d]pyrimidin-7-one

HRID 387215Notes

Reaction equation

HRID 387215 reaction equation
[Br:1][C:2]1[C:13](=[O:14])[N:12]([CH2:15][CH3:16])[C:5]2[N:6]=[C:7]([S:10][CH3:11])[N:8]=[CH:9][C:4]=2[CH:3]=1.ClC1C=CC=C(C(OO)=[O:25])C=1>ClCCl>[Br:1][C:2]1[C:13](=[O:14])[N:12]([CH2:15][CH3:16])[C:5]2[N:6]=[C:7]([S:10]([CH3:11])=[O:25])[N:8]=[CH:9][C:4]=2[CH:3]=1

Participants

4

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 667603446-Bromo-8-ethyl-2-methylsulfanylpyrido[2,3-d]pyrimidin-7-one

Product 1

HCID 671196106-Bromo-8-ethyl-2-methylsulfinylpyrido[2,3-d]pyrimidin-7-one

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
2.5 °C

Procedure

To a solution of 6-bromo-8-ethyl-2-methylsulfanyl-8H-pyrido[2,3-d]pyrimidin-7-one (3, 0.96 g, 3.19 mmol) in dichloromethane (40 mL) was added 3-chloroperbenzoic acid (77%, 0.68 g, 3.04 mmol) in dichloromethane (10 mL) at 0-5° C. and the mixture was stirred at 0-5° C. for 1 h. The reaction mixture was washed with 10% sodium bicarbonate solution (1×20 mL) and water (1×20 mL). The organic layer was dried over sodium sulfate, filtered and evaporated. The title compound was obtained as a pale yellow solid (0.98 g, 3.10 mmol, 97%). ESMS m/z 316 (M+H)+.

Workup

  1. washThe reaction mixture was washed with 10% sodium bicarbonate solution (1×20 mL) and water (1×20 mL)
  2. dry with materialThe organic layer was dried over sodium sulfate
  3. filtrationfiltered
  4. customevaporated

Sources & evidence

ORD record
ord-c4554730187243f094dcff3a1a14327d
Source dataset
uspto-grants-2013_02
Patent number
US08372970B2

Reaction notes

Loading…