Hydrogen Peroxide → 5-chloro-4-(5-cyclopropyl-1H-pyrazol-3-ylamino)pyrimidine-2-carboxamide

HRID 1484991Notes

Reaction equation

HRID 1484991 reaction equation
[Cl:1][C:2]1[C:3]([NH:10][C:11]2[CH:15]=[C:14]([CH:16]3[CH2:18][CH2:17]3)[NH:13][N:12]=2)=[N:4][C:5]([C:8]#[N:9])=[N:6][CH:7]=1.C([O-])([O-])=[O:20].[K+].[K+].OO.O>CS(C)=O>[Cl:1][C:2]1[C:3]([NH:10][C:11]2[CH:15]=[C:14]([CH:16]3[CH2:17][CH2:18]3)[NH:13][N:12]=2)=[N:4][C:5]([C:8]([NH2:9])=[O:20])=[N:6][CH:7]=1

Participants

6

Reactant 4

HCID 784Hydrogen PeroxideHCID 962WaterHCID 11430Potassium CarbonateHCID 669276695-chloro-4-(5-cyclopropyl-1H-pyrazol-3-ylamino)pyrimidine-2-carbonitrile

Product 1

HCID 581693985-chloro-4-(5-cyclopropyl-1H-pyrazol-3-ylamino)pyrimidine-2-carboxamideYield 89%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

The mixture of 5-chloro-4-(5-cyclopropyl-1H-pyrazol-3-ylamino)pyrimidine-2-carbonitrile (1.0 g, 3.85 mmol, 1.0 eq) and K2CO3 (2.0 g, 14.49 mmol, 3.8 eq) in DMSO (20 mL) was stirred at room temperature, and 30% hydrogen peroxide (3 mL) was added dropwise. The reaction mixture was stirred at rt for 1 h, water was added and the suspension was filtered to afford 5-chloro-4-(5-cyclopropyl-1H-pyrazol-3-ylamino)pyrimidine-2-carboxamide (950 mg, 89%). LC-MS (m/z)=279.0 [M+H]+.

Workup

  1. stirringThe reaction mixture was stirred at rt for 1 h
  2. filtrationthe suspension was filtered

Sources & evidence

ORD record
ord-010a4b60709744eca030856e8e0a9be5
Source dataset
uspto-grants-2016_08
Patent number
US09422271B2

Reaction notes

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