Ammonia → 5-Amino-pyrazolo[1,5-a]pyrimidine-3-carboxylic acid (2-methyl-4-o-tolyl-thiazol-5-yl)-amide

HRID 474356Notes

Reaction equation

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

Participants

Conditions

Temperature: 120 °C

Procedure

A mixture of 5-chloro-pyrazolo[1,5-a]pyrimidine-3-carboxylic acid (2-methyl-4-o-tolyl-thiazol-5-yl)-amide (74.0 mg, 0.19 mmol, 1.0 equiv) and 2M ammonia in propan-2-ol (3 mL) was sealed and heated in a microwave reactor at 120° C. for 1 hour. The solvent was removed under vacuum, and the resultant residue purified by flash column chromatography on silica gel (gradient: 0 to 5% methanol in dichloromethane) to afford 11.0 mg (16%) of 5-amino-pyrazolo[1,5-a]pyrimidine-3-carboxylic acid (2-methyl-4-o-tolyl-thiazol-5-yl)-amide. LCMS (ESI) m+H=365.1; 1H NMR (400 MHz, DMSO-d6) δ: 10.35 (s, 1H), 8.66 (d, 1H), 8.23 (s, 1H), 7.47-7.37 (m, 4H), 6.38 (d, 1H), 2.61 (s, 3H), 2.20 (s, 3H).

Workup

customwas sealed
customThe solvent was removed under vacuum
customthe resultant residue purified by flash column chromatography on silica gel (gradient: 0 to 5% methanol in dichloromethane)

Sources & evidence

ORD record: ord-5fa215685e7f4519a7b079abd3a20c60
Source dataset: uspto-grants-2014_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08637526B2

Reaction notes

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