Ammonia → 5-amino-pyrazolo[1,5-a]pyrimidine-3-carboxylic acid [5-(5-chloro-2-difluoromethoxy-phenyl)-1-(2-trimethylsilanyl-ethoxymethyl)-1H-pyrazol-4-yl]-amide

HRID 529760Notes

Reaction equation

[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([O:34][CH:35]([F:37])[F:36])=[C:6]([C:8]2[N:12]([CH2:13][O:14][CH2:15][CH2:16][Si:17]([CH3:20])([CH3:19])[CH3:18])[N:11]=[CH:10][C:9]=2[NH:21][C:22]([C:24]2[CH:25]=[N:26][N:27]3[CH:32]=[CH:31][C:30](Cl)=[N:29][C:28]=23)=[O:23])[CH:7]=1.[NH3:38]>C1COCC1>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([O:34][CH:35]([F:36])[F:37])=[C:6]([C:8]2[N:12]([CH2:13][O:14][CH2:15][CH2:16][Si:17]([CH3:18])([CH3:20])[CH3:19])[N:11]=[CH:10][C:9]=2[NH:21][C:22]([C:24]2[CH:25]=[N:26][N:27]3[CH:32]=[CH:31][C:30]([NH2:38])=[N:29][C:28]=23)=[O:23])[CH:7]=1

Participants

Conditions

Temperature: 50 °C

Procedure

5-chloro-pyrazolo[1,5-a]pyrimidine-3-carboxylic acid [5-(5-chloro-2-difluoromethoxy-phenyl)-1-(2-trimethylsilanyl-ethoxymethyl)-1H-pyrazol-4-yl]-amide (756 mg, 1.32 mmol) was dissolved in THF (10 mL) and concentrated aqueous ammonia (10 mL) added. The mixture was heated at 50° C. for 3 hours then allowed to cool to ambient temperature. The solvent was evaporated and the residue azeotroped with methanol (×2) to afford 5-amino-pyrazolo[1,5-a]pyrimidine-3-carboxylic acid [5-(5-chloro-2-difluoromethoxy-phenyl)-1-(2-trimethylsilanyl-ethoxymethyl)-1H-pyrazol-4-yl]-amide as a white solid (724 mg, 99%). LCMS (Method 4) [M+H]+=549.9, RT=4.11 min.

Workup

temperatureto cool to ambient temperature
customThe solvent was evaporated
customthe residue azeotroped with methanol (×2)

Sources & evidence

ORD record: ord-79f6d97296b54cf5a8639d59c28ceff4
Source dataset: uspto-grants-2016_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09346815B2

Reaction notes

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