Potassium hydroxy sulfite → HCID 178428229, compound

HRID 1091817Notes

Reaction equation

HRID 1091817 reaction equation
[Cl:1][C:2]1[N:7]=[C:6]([S:8]([CH3:10])=[O:9])[N:5]=[C:4]([NH:11][C:12]2[NH:16][N:15]=[C:14]([CH3:17])[CH:13]=2)[CH:3]=1.[OH:18]OS([O-])=O.[K+]>CO.O>[Cl:1][C:2]1[N:7]=[C:6]([S:8]([CH3:10])(=[O:18])=[O:9])[N:5]=[C:4]([NH:11][C:12]2[NH:16][N:15]=[C:14]([CH3:17])[CH:13]=2)[CH:3]=1

Participants

5

Reactant 2

HCID 23707502Potassium hydroxy sulfiteHCID 178428228HCID 178428228, compound

Product 1

HCID 178428229HCID 178428229, compoundYield 88%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Conditions

Temperature
0 °C

Procedure

To a stirred suspension of 6-chloro-N-(3-methyl-1H-pyrazol-5-yl)-2-(methylsulfinyl)pyrimidin-4-amine (8 g, 31.2 mmol) in methanol (200 ml) at 0° C. was added a suspension of Oxone (44 g, 71.7 mmol) in water (100 ml) portionwise over 10 minutes. The mixture was stirred for 30 minutes at 0° C. then warmed to ambient and stirred for an additional 2 hours. The reaction mixture was filtered and the resulting solid slurried in aqueous sodium bicarbonate. The mixture was filtered and the solid washed with water, then diethyl ether. The solid was slurried in ethyl acetate, filtered and dried. This gave the title product as an off-white solid (7.9 g, 88%); 1H NMR (d6-DMSO) δ 2.24 (3H, s), 3.35 (3H, s), 5.85 (0.5H, brs), 6.50 (0.5H, brs), 6.95 (0.5H, brs), 8.00 (0.5H, brs), 10.95 (1H, s), 12.28 (1H, s); MS ES+ 288.07, ES− 286.25.

Workup

  1. additionwas added
  2. temperaturethen warmed
  3. stirringstirred for an additional 2 hours
  4. filtrationThe reaction mixture was filtered
  5. filtrationThe mixture was filtered
  6. washthe solid washed with water
  7. filtrationfiltered
  8. customdried

Sources & evidence

ORD record
ord-64774e7c56664a74bcafb5b461c000bd
Source dataset
uspto-grants-2012_03
Patent number
US08129399B2

Reaction notes

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