Bicarbonate Ion → HCID 178428229, compound

HRID 1253812Notes

Reaction equation

HRID 1253812 reaction equation
[Cl:1][C:2]1[N:7]=[C:6](SC)[N:5]=[C:4]([NH:10][C:11]2[NH:15][N:14]=[C:13]([CH3:16])[CH:12]=2)[CH:3]=1.O[O:18][S:19]([O-:21])=O.[K+].[C:23](=O)(O)[O-]>CO.O>[Cl:1][C:2]1[N:7]=[C:6]([S:19]([CH3:23])(=[O:21])=[O:18])[N:5]=[C:4]([NH:10][C:11]2[NH:15][N:14]=[C:13]([CH3:16])[CH:12]=2)[CH:3]=1

Participants

6

Reactant 3

HCID 769Bicarbonate IonHCID 23707502Potassium hydroxy sulfiteHCID 178418729HCID 178418729, compound

Product 1

HCID 178428229HCID 178428229, compoundYield 80%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent2×

Procedure

To a stirred solution of 6-chloro-N-(3-methyl-1H-pyrazol-5-yl)-2-(methylthio)pyrimidin-4-amine (8 g, 31.19 mmol) in MeOH (200 ml) cooled in an ice bath was added portionwise a slurry of oxone (44 g, 71.73 mmol) in water (100 ml) over 10 minutes. The reaction mixture was stirred at this temperature for a further 30 minutes before being allowed to warm up to room temperature for 2 hours. The solid, isolated by filtration, was stirred vigorously in a 1:1 mixture of water and saturated bicarbonate solution. The solid was then filtered and dried in a pistol under vacuo to afford the title compound as a yellow solid (7.17 g, 80% yield). 1H NMR (DMSO D6, 400 MHz) δ2.23 (3H, s), 3.32 (3H, s), 5.80-8.10 (2H, br m), 10.92 (1H, br s), 12.26 (1H, br s); MS (ES+) 288, (ES−) 286.

Workup

  1. customThe solid, isolated by filtration
  2. filtrationThe solid was then filtered
  3. customdried in a pistol under vacuo

Sources & evidence

ORD record
ord-85268789e66e412dbf87898f4bd05a19
Source dataset
uspto-grants-2013_06
Patent number
US08455507B2

Reaction notes

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