Lithium Hydroxide → Lithium 6-fluoropyrazolo[1,5-a]pyrimidine-3-carboxylate

HRID 418283Notes

Reaction equation

HRID 418283 reaction equation
[F:1][C:2]1[CH:3]=[N:4][C:5]2[N:6]([N:8]=[CH:9][C:10]=2[C:11]([O:13]CC)=[O:12])[CH:7]=1.[OH-].[Li+:17]>O.CO.C1COCC1>[F:1][C:2]1[CH:3]=[N:4][C:5]2[N:6]([N:8]=[CH:9][C:10]=2[C:11]([O-:13])=[O:12])[CH:7]=1.[Li+:17]

Participants

6

Reactant 2

HCID 3939Lithium HydroxideHCID 59152099Ethyl 6-fluoropyrazolo[1,5-a]pyrimidine-3-carboxylate

Product 1

HCID 66649478Lithium 6-fluoropyrazolo[1,5-a]pyrimidine-3-carboxylateYield 108.4%

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

A suspension of ethyl 6-fluoropyrazolo[1,5-a]pyrimidine-3-carboxylate (512 mg, 2.45 mmol) and lithium hydroxide (61.5 mg, 2.57 mmol) in water (1 ml), MeOH (1 ml) and THF (1 ml) was irradiated to 100° C. for 10 min in the microwave. The reaction mixture was concentrated under vacuum, azeotroping with toluene (10 ml) to leave the title compound as a yellow powder (497 mg). This crude material was used directly in the subsequent reactions.

Workup

  1. customwas irradiated to 100° C. for 10 min in the microwave
  2. concentrationThe reaction mixture was concentrated under vacuum
  3. customazeotroping with toluene (10 ml)

Sources & evidence

ORD record
ord-78e4efa998b94c459cd95d3d3dfe2962
Source dataset
uspto-grants-2012_01
Patent number
US08093249B2

Reaction notes

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