7-[3-(Trifluoromethyl)phenyl]pyrazolo[1,5-a]pyrimidine-3-carbonitrile → HCID 135773307, compound

HRID 231510

Reaction equation

HRID 231510 reaction equation
[F:1][C:2]([F:21])([F:20])[C:3]1[CH:8]=[CH:7][CH:6]=[C:5]([C:9]2[N:14]3[N:15]=[CH:16][C:17]([C:18]#[N:19])=[C:13]3[N:12]=[CH:11][CH:10]=2)[CH:4]=1.C([BH3-])#N.[Na+]>C(O)(=O)C>[F:20][C:2]([F:1])([F:21])[C:3]1[CH:4]=[C:5]([C:9]2[N:14]3[N:15]=[CH:16][C:17]([C:18]#[N:19])=[C:13]3[NH:12][CH2:11][CH:10]=2)[CH:6]=[CH:7][CH:8]=1

Participants

4

Reactant 2

HCID 27410147-[3-(Trifluoromethyl)phenyl]pyrazolo[1,5-a]pyrimidine-3-carbonitrileHCID 5003444Sodium cyanoborohydride

Product 1

HCID 135773307HCID 135773307, compound

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

To a solution of 6.0 g of 7-(α,α,α-trifluoro-m-tolyl)pyrazolo[1,5-a]pyrimidine-3-carbonitrile (Ex. 3, U.S. Pat. No. 4,236,005) in 100 ml of glacial acetic acid, was added in portions, 3.0 g of sodium cyanoborohydride at room temperature under nitrogen. The mixture was stirred at room temperature for 2 hours. The precipitate was collected by filtration, washed with water, then dissolved in dichloromethane. The organic solution was neutralized with a saturated solution of sodium bicarbonate, then dried over anhydrous sodium sulfate and filtered. The filtrate was evaporated in vacuo and gave the desired product as a white solid. The product was recrystallized from isopropyl alcohol, mp 175°-177° C.

Workup

  1. filtrationThe precipitate was collected by filtration
  2. washwashed with water
  3. dissolutiondissolved in dichloromethane
  4. dry with materialdried over anhydrous sodium sulfate
  5. filtrationfiltered
  6. customThe filtrate was evaporated in vacuo

Sources & evidence

ORD record
ord-8031aa026700490d9a59d611704f7ea8
Source dataset
uspto-grants-1989_07
Patent number
US04847256

Linked notes

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