Ammonia → Pyrazolo[1,5-a]pyrimidine-3-carboxamide, 5-amino-N-[3-(2,5-dichlorophenyl)-1-methyl-1H-pyrazol-4-yl]-

HRID 474345Notes

Reaction equation

HRID 474345 reaction equation
Cl[C:2]1[CH:7]=[CH:6][N:5]2[N:8]=[CH:9][C:10]([C:11]([NH:13][C:14]3[C:15]([C:20]4[CH:25]=[C:24]([Cl:26])[CH:23]=[CH:22][C:21]=4[Cl:27])=[N:16][N:17]([CH3:19])[CH:18]=3)=[O:12])=[C:4]2[N:3]=1.[NH3:28]>C(O)C>[Cl:27][C:21]1[CH:22]=[CH:23][C:24]([Cl:26])=[CH:25][C:20]=1[C:15]1[C:14]([NH:13][C:11]([C:10]2[CH:9]=[N:8][N:5]3[CH:6]=[CH:7][C:2]([NH2:28])=[N:3][C:4]=23)=[O:12])=[CH:18][N:17]([CH3:19])[N:16]=1

Participants

4

Reactant 2

HCID 222AmmoniaHCID 580630965-chloro-N-(3-(2,5-dichlorophenyl)-1-methyl-1H-pyrazol-4-yl)pyrazolo[1,5-a]pyrimidine-3-carboxamide

Product 1

HCID 58063117Pyrazolo[1,5-a]pyrimidine-3-carboxamide, 5-amino-N-[3-(2,5-dichlorophenyl)-1-methyl-1H-pyrazol-4-yl]-Yield 77%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of 5-chloro-N-(3-(2,5-dichlorophenyl)-1-methyl-1H-pyrazol-4-yl)pyrazolo[1,5-a]pyrimidine-3-carboxamide (110 mg, 0.26 mmol) in ethanol saturated with ammonia (4 mL) was heated at 95° C. for 30 minutes with microwave irradiation. The mixture was concentrated. Purification by flash column chromatography afforded 5-amino-pyrazolo[1,5-a]pyrimidine-3-carboxylic acid [3-(2,5-dichloro-phenyl)-1-methyl-1H-pyrazol-4-yl]-amide as a solid (80 mg, 77% yield). 1H NMR (400 MHz, DMSO-d6): 9.37 (s, 1H), 8.63 (d, J=7.6 Hz, 1H), 8.14-8.16 (m, 2H), 7.70 (m, 1H), 7.52-7.55 (m, 2H), 6.39 (d, J=8.0 Hz, 1H), 3.91 (s, 3H).

Workup

  1. concentrationThe mixture was concentrated
  2. customPurification by flash column chromatography

Sources & evidence

ORD record
ord-6cf7303bbb144884bf7b06e6c4bc35ae
Source dataset
uspto-grants-2014_01
Patent number
US08637526B2

Reaction notes

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