Triethylamine → 5-(4-Chloro-phenyl)-pyrazolo[1,5-a]pyrimidine

HRID 558557Notes

Reaction equation

HRID 558557 reaction equation
Cl[C:2]1[N:7]2[N:8]=[CH:9][CH:10]=[C:6]2[N:5]=[C:4]([C:11]2[CH:16]=[CH:15][C:14]([Cl:17])=[CH:13][CH:12]=2)[CH:3]=1.C(N(CC)CC)C.[H][H]>CCO.[Pd]>[Cl:17][C:14]1[CH:13]=[CH:12][C:11]([C:4]2[CH:3]=[CH:2][N:7]3[N:8]=[CH:9][CH:10]=[C:6]3[N:5]=2)=[CH:16][CH:15]=1

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 210357027-Chloro-5-(4-chlorophenyl)pyrazolo[1,5-a]pyrimidineHCID 178418361HCID 178418361, compound

Product 1

HCID 670008375-(4-Chloro-phenyl)-pyrazolo[1,5-a]pyrimidineYield 67.5%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A mixture of 7-chloro-5-(4-chloro-phenyl)-pyrazolo[1,5-a]pyrimidine (example C.5, step 2) (1.06 g, 4.0 mmol), triethylamine (0.84 mL), and 5% Pd—C (0.1 g) in EtOH (40 mL) was stirred in an atmosphere of hydrogen for 1.5 h. The catalyst was filtered off, the solution was evaporated in vacuo and the residue was crystallized from EtOAc/cyclohexane to give 5-(4-chloro-phenyl)-pyrazolo[1,5-a]pyrimidine (0.62 g, 67%) as a pale-yellow solid. MS (ISP) 230.4 [(M+H)+]; mp 178-180° C.

Workup

  1. filtrationThe catalyst was filtered off
  2. customthe solution was evaporated in vacuo
  3. customthe residue was crystallized from EtOAc/cyclohexane

Sources & evidence

ORD record
ord-e526dbd0a5cc4a40bc67b11cb4ddb542
Source dataset
uspto-grants-2011_11
Patent number
US08063048B2

Reaction notes

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