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

HRID 268995Notes

Reaction equation

HRID 268995 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-b100907883954291834e788b580d3cf5
Source dataset
uspto-grants-2008_11
Patent number
US07446113B2

Reaction notes

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