Ammonium Hydroxide → 5-amino-N-(1-(3-chlorophenyl)-3-methyl-1H-pyrazol-5-yl)pyrazolo[1,5-a]pyrimidine-3-carboxamide
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[N:18]([C:19]4[CH:24]=[CH:23][CH:22]=[C:21]([Cl:25])[CH:20]=4)[N:17]=[C:16]([CH3:26])[CH:15]=3)=[O:12])=[C:4]2[N:3]=1.[OH-].[NH4+:28]>>[NH2:28][C:2]1[CH:7]=[CH:6][N:5]2[N:8]=[CH:9][C:10]([C:11]([NH:13][C:14]3[N:18]([C:19]4[CH:24]=[CH:23][CH:22]=[C:21]([Cl:25])[CH:20]=4)[N:17]=[C:16]([CH3:26])[CH:15]=3)=[O:12])=[C:4]2[N:3]=1Participants
Conditions
- Temperature
- 105 °C
Procedure
A mixture of 74% pure 5-chloro-N-(1-(3-chlorophenyl)-3-methyl-1H-pyrazol-5-yl)pyrazolo[1,5-a]pyrimidine-3-carboxamide (55 mg, 0.14 mM, 1.0 equiv) and 3 mL of concentrated ammonium hydroxide was sealed and heated in a microwave reactor at 105° C. for 30 minutes. The reaction mixture was cooled and the precipitated product collected by filtration to give 25 mg (48%) of 5-amino-N-(1-(3-chlorophenyl)-3-methyl-1H-pyrazol-5-yl)pyrazolo[1,5-a]pyrimidine-3-carboxamide which was purified by reverse phase chromatography on C-18 with acetonitrile/water (0 to 60 gradient, 0.1% TFA) and lyophilized. LCMS (ESI) m+H=368.3 (one chlorine isotope pattern), 1H NMR (400 MHz, DMSO-d6) δ: 9.94 (s, 1H), 8.66 (d, 1H), 8.20 (s, 1H) 7.67 (s, 1H), 7.57 (d, 1H), 7.49 (dd, 1H), 7.44 (d, 1H), 6.89 (br s, 1H), 6.40 (overlapping d and s, 2H), 2.26 (s, 3H).
Workup
- customwas sealed
- temperatureThe reaction mixture was cooled
- filtrationthe precipitated product collected by filtration
Sources & evidence
- ORD record
- ord-378542327ff54d8b9eec7416b2b9c89f
- Source dataset
- uspto-grants-2014_01
- Patent number
- US08637526B2
Reaction notes
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