Acetic Acid → 5-Chloro-6-phenylpyrazolo[1,5-a]pyrimidine

HRID 1851190Notes

Reaction equation

HRID 1851190 reaction equation
[Cl:1][C:2]1[C:7]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)=[C:6](Cl)[N:5]2[N:15]=[CH:16][CH:17]=[C:4]2[N:3]=1.C(O)(=O)C.CO>C1COCC1>[Cl:1][C:2]1[C:7]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)=[CH:6][N:5]2[N:15]=[CH:16][CH:17]=[C:4]2[N:3]=1

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 887MethanolHCID 594278075,7-Dichloro-6-phenylpyrazolo[1,5-a]pyrimidine

Product 1

HCID 866306645-Chloro-6-phenylpyrazolo[1,5-a]pyrimidine

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
50 °C

Procedure

A mixture of 1 g 5,7-dichloro-6-phenylpyrazolo[1,5-a]pyrimidine, 0.5 mL glacial acetic acid, 1 mL methanol, 6 mL THF and 730 mg of Zn/Cu pair were stirred for 3 h at 50° C. The mixture was filtered through celite, evaporated to dryness and the residue was purified on silica gel (hexanes/ethyl acetate) to yield 550 mg of a 1:1 mixture of the desired product and the starting material, which was used without further purification.

Workup

  1. filtrationThe mixture was filtered through celite
  2. customevaporated to dryness
  3. customthe residue was purified on silica gel (hexanes/ethyl acetate)
  4. customto yield

Sources & evidence

ORD record
ord-b4d00eedd7ab447eb3b1f032aabe153a
Source dataset
uspto-grants-2015_02
Patent number
US08957064B2

Reaction notes

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