4-amino-N,1-dimethyl-1H-pyrazole-5-carboxamide → 5-Bromo-2-isopropyl-pyrimidine-4-carboxylic acid (1-methyl-5-methylcarbamoyl-1H-pyrazol-4-yl)-amide

HRID 467751Notes

Reaction equation

HRID 467751 reaction equation
[Br:1][C:2]1[C:3]([C:11]([OH:13])=O)=[N:4][C:5]([CH:8]([CH3:10])[CH3:9])=[N:6][CH:7]=1.[CH3:14][NH:15][C:16]([C:18]1[N:19]([CH3:24])[N:20]=[CH:21][C:22]=1[NH2:23])=[O:17]>>[CH3:24][N:19]1[C:18]([C:16](=[O:17])[NH:15][CH3:14])=[C:22]([NH:23][C:11]([C:3]2[C:2]([Br:1])=[CH:7][N:6]=[C:5]([CH:8]([CH3:9])[CH3:10])[N:4]=2)=[O:13])[CH:21]=[N:20]1

Participants

3

Reactant 2

HCID 64853704-amino-N,1-dimethyl-1H-pyrazole-5-carboxamideHCID 672998985-Bromo-2-(propan-2-yl)pyrimidine-4-carboxylic acid

Product 1

HCID 866601955-Bromo-2-isopropyl-pyrimidine-4-carboxylic acid (1-methyl-5-methylcarbamoyl-1H-pyrazol-4-yl)-amide

Procedure

The product was obtained starting from 5-bromo-2-isopropyl-pyrimidine-4-carboxylic acid (intermediate A-4, step 1; 300 mg, 1.22 mmol) and 4-amino-2-methyl-2H-pyrazole-3-carboxylic acid methylamide (245 mg, 1.59 mmol) according to the method described in example 64, step 6 after extraction with ethyl acetate and purification by silica gel chromatography using ethyl acetate as light brown solid (472 mg, 96%).

Workup

  1. customThe product was obtained
  2. extractionafter extraction
  3. customwith ethyl acetate and purification by silica gel chromatography

Sources & evidence

ORD record
ord-ad7fdc108f4b4610bf463fc8d07400c1
Source dataset
uspto-grants-2014_01
Patent number
US08623866B2

Reaction notes

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