Phosphorus oxychloride → HCID 19022408, compound

HRID 846895Notes

Reaction equation

HRID 846895 reaction equation
O[C:2]1[CH:7]=[C:6]([C:8]([F:11])([F:10])[F:9])[N:5]2[N:12]=[CH:13][C:14]([C:15]([O:17][CH3:18])=[O:16])=[C:4]2[N:3]=1.P(Cl)(Cl)([Cl:21])=O>CN(C)C1C=CN=CC=1>[Cl:21][C:2]1[CH:7]=[C:6]([C:8]([F:11])([F:10])[F:9])[N:5]2[N:12]=[CH:13][C:14]([C:15]([O:17][CH3:18])=[O:16])=[C:4]2[N:3]=1

Participants

4

Reactant 2

HCID 24813Phosphorus oxychlorideHCID 178498898HCID 178498898, compound

Product 1

HCID 19022408HCID 19022408, compound

Reagents, catalysts & solvents 1

HCID 142844-(Dimethylamino)pyridineCatalyst

Procedure

A mixture of 2.70 g of methyl 5-hydroxy-7-(trifluoromethyl)pyrazolo[1,5-a]pyrimidine-3-carboxylate and 1.26 g of 4-dimethylaminopyridine was heated to 100° for 2.5 hours in 50 ml of phosphorus oxychloride. The resulting solution was concentrated in a vacuum and then partitioned between ethyl acetate and saturated sodium chloride solution. The organic phase was washed in succession with 1N hydrochloric acid and saturated sodium chloride solution, dried over sodium sulphate, freed from solvent in a vacuum and the residue was crystallized from ethyl acetate/petroleum ether. There was obtained methyl 5-chloro-7-(tri-fluoromethyl)pyrazolo[1,5-a]pyrimidine-3-carboxylate as white crystals of m.p. 126°-127°.

Workup

  1. concentrationThe resulting solution was concentrated in a vacuum
  2. custompartitioned between ethyl acetate and saturated sodium chloride solution
  3. washThe organic phase was washed in succession with 1N hydrochloric acid and saturated sodium chloride solution
  4. dry with materialdried over sodium sulphate
  5. customthe residue was crystallized from ethyl acetate/petroleum ether

Sources & evidence

ORD record
ord-e77e3d35f8a3457d8f0b4c0748659488
Source dataset
uspto-grants-1992_08
Patent number
US05138066

Reaction notes

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