Ethyl Acetate → 4,5,6,7-Tetrahydro-7-[3-(trifluoromethyl)phenyl]pyrazolo[1,5-a]pyrimidine-3-carbonitrile

HRID 231517Notes

Reaction equation

HRID 231517 reaction equation
[F:1][C:2]([F:21])([F:20])[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.C(OCC)(=O)C>[Pd].C(O)(=O)C>[F:20][C:2]([F:1])([F:21])[C:3]1[CH:4]=[C:5]([CH:9]2[N:14]3[N:15]=[CH:16][C:17]([C:18]#[N:19])=[C:13]3[NH:12][CH2:11][CH2:10]2)[CH:6]=[CH:7][CH:8]=1

Participants

5

Reactant 2

HCID 8857Ethyl AcetateHCID 1357733074,5-Dihydro-7-[3-(trifluoromethyl)phenyl]pyrazolo[1,5-a]pyrimidine-3-carbonitrile

Product 1

HCID 1356713744,5,6,7-Tetrahydro-7-[3-(trifluoromethyl)phenyl]pyrazolo[1,5-a]pyrimidine-3-carbonitrile

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 176Acetic AcidSolvent

Procedure

A mixture of 1.5 parts of 4,5-dihydro-7-[3-(trifluoromethyl)phenyl]pyrazolo[1,5-a]pyrimidine-3-carbonitrile, 50 parts of ethyl acetate, 10 parts of acetic acid and 0.2 parts of 5% palladium-on-carbon catalyst was shaken on a Parr hydrogenator under about 30 pounds of hydrogen pressure for 4.5 hours. The reaction mixture was filtered, and the mother liquor was concentrated to remove the solvent. The yellow oil which was obtained was crystallized by trituration in ether. The crystalline product was recrystallized from ethyl acetate by addition of hexane. The product 4,5,6,7-tetrahydro-7-[3-(trifluoromethyl)phenyl]pyrazolo[1,5-a]pyrimidine-3-carbonitrile melted at 181°-183° C.

Workup

  1. filtrationThe reaction mixture was filtered
  2. concentrationthe mother liquor was concentrated
  3. customto remove the solvent
  4. customThe yellow oil which was obtained
  5. customwas crystallized by trituration in ether
  6. customThe crystalline product was recrystallized from ethyl acetate by addition of hexane

Sources & evidence

ORD record
ord-31b048f485c9492a82c4ed710518aa9a
Source dataset
uspto-grants-1989_07
Patent number
US04847256

Reaction notes

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