Triethylsilane → 4,5,6,7-Tetrahydro-7-[3-(trifluoromethyl)phenyl]pyrazolo[1,5-a]pyrimidine-3-carboxamide

HRID 231512

Reaction equation

[F:1][C:2]([F:22])([F:21])[C:3]1[CH:4]=[C:5]([C:9]2[N:14]3[N:15]=[CH:16][C:17]([C:18]([NH2:20])=[O:19])=[C:13]3[NH:12][CH2:11][CH:10]=2)[CH:6]=[CH:7][CH:8]=1.C([SiH](CC)CC)C.[OH-].[K+]>FC(F)(F)C(O)=O>[F:21][C:2]([F:1])([F:22])[C:3]1[CH:4]=[C:5]([CH:9]2[N:14]3[N:15]=[CH:16][C:17]([C:18]([NH2:20])=[O:19])=[C:13]3[NH:12][CH2:11][CH2:10]2)[CH:6]=[CH:7][CH:8]=1

Participants

Conditions

Temperature: 60 °C

Procedure

A solution of 3.44 g of 4,5-dihydro-7-[3-(trifluoromethyl)phenyl]pyrazolo[1,5-a]pyrimidine-3-carboxamide (Ex. 24) in 40 ml of trifluoroacetic acid was stirred under nitrogen and heated to 60° C. in an oil bath. Then 5.0 ml of triethylsilane was added and the mixture was stirred at 60° C. for 24 hours. The reaction mixture was cooled and carefully poured into a beaker containing a 25% aqueous solution of potassium hydroxide and cracked ice. The product which precipitated was extracted into chloroform. The chloroform was washed with water, dried over anhydrous sodium sulfate and filtered. The filtrate was evaporated in vacuo and gave crystals which were recrystallized from toluene-hexane to give the desired product, mp 152°-154° C.

Workup

temperatureThe reaction mixture was cooled
additioncarefully poured into a beaker
customThe product which precipitated
extractionwas extracted into chloroform
washThe chloroform was washed with water
dry with materialdried over anhydrous sodium sulfate
filtrationfiltered
customThe filtrate was evaporated in vacuo
customgave crystals which
customwere recrystallized from toluene-hexane

Sources & evidence

ORD record: ord-eec79a0350064775b60e18124d16bc30
Source dataset: uspto-grants-1989_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04847256

Linked notes

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