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

HRID 1915546Notes

Reaction equation

HRID 1915546 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 are stirred for 3 h at 50° C. The mixture is filtered through celite, evaporated to dryness and the residue is 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 is filtered through celite
  2. customevaporated to dryness
  3. customthe residue is purified on silica gel (hexanes/ethyl acetate)
  4. customto yield

Sources & evidence

ORD record
ord-4449321a44404b87807073699c9f4a98
Source dataset
uspto-grants-2013_12
Patent number
US08614218B2

Reaction notes

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