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

HRID 2050508

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 (Example 8) in 40 ml of trifluoroacetic acid is stirred under nitrogen and heated to 60° C. in an oil bath. Then 5.0 ml of triethylsilane is added and the mixture is stirred at 60° C. for 24 hours. The reaction mixture is cooled and carefully poured into a beaker containing a 25 percent aqueous solution of potassium hydroxide and cracked ice. The product which precipitates is extracted into chloroform, and the extract is washed with water, dried over anhydrous sodium sulfate and filtered. The filtrate is evaporated in vacuo to give crystals which are then recrystallized from toluene-hexane to give the desired product, mp 152-154° C.

Workup

temperatureThe reaction mixture is cooled
additioncarefully poured into a beaker
customThe product which precipitates
extractionis extracted into chloroform
washthe extract is washed with water
dry with materialdried over anhydrous sodium sulfate
filtrationfiltered
customThe filtrate is evaporated in vacuo
customto give crystals which
customare then recrystallized from toluene-hexane

Sources & evidence

ORD record: ord-e7de8176c5cc45b6b607074fc86f9053
Source dataset: uspto-grants-1991_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05013737

Linked notes

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