Pyrazol-3-ylamine → 5-(3,4-Dichlorophenyl)-7-(trifluoromethyl)pyrazolo[1,5-a]pyrimidine

HRID 2237859

Reaction equation

[N:1]1[NH:2][C:3]([NH2:6])=[CH:4][CH:5]=1.[Cl:7][C:8]1[CH:9]=[C:10]([C:15](=O)[CH2:16][C:17](=O)[C:18]([F:21])([F:20])[F:19])[CH:11]=[CH:12][C:13]=1[Cl:14]>C(O)(=O)C>[Cl:7][C:8]1[CH:9]=[C:10]([C:15]2[CH:16]=[C:17]([C:18]([F:21])([F:19])[F:20])[N:2]3[N:1]=[CH:5][CH:4]=[C:3]3[N:6]=2)[CH:11]=[CH:12][C:13]=1[Cl:14]

Participants

Conditions

Temperature: 0 °C

Procedure

A mixture of 2H-pyrazol-3-ylamine (4.0 g, 48 mmol) and 1-(3,4-dichloro-phenyl)-4,4,4-trifluoro-butane-1,3-dione (11.4 g, 40 mmol) in acetic acid (80 mL) was heated at reflux for 4 h. The solution was poured into ice-cold 10% aqueous ammonia and the mixture was stirred at 0° C. for 0.5 h. The solid was isolated by filtration, triturated with EtOH (40 mL), and dried to give 5-(3,4-dichloro-phenyl)-7-trifluoromethyl-pyrazolo[1,5-a]pyrimidine as a pale-yellow solid. MS (ISP) 332.1[(M+H)+]; mp 130-131° C.

Workup

temperaturewas heated
temperatureat reflux for 4 h
customThe solid was isolated by filtration
customtriturated with EtOH (40 mL)
customdried

Sources & evidence

ORD record: ord-82ede27ffffd4af1b87508007a133a58
Source dataset: uspto-grants-2010_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07718661B2

Linked notes

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