Hydrochloric Acid → 2-(4-Fluorophenyl)-3-(pyridin-4-yl)-4,5,6,7-tetrahydropyrazolo[1,5-a]pyrimidine hydrochloride

HRID 54954Notes

Reaction equation

HRID 54954 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:16]([C:17]3[CH:22]=[CH:21][N:20]=[CH:19][CH:18]=3)=[C:11]3[NH:12][CH2:13][CH2:14][CH2:15][N:10]3[N:9]=2)=[CH:4][CH:3]=1.[ClH:23]>C(O)C>[ClH:23].[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:16]([C:17]3[CH:22]=[CH:21][N:20]=[CH:19][CH:18]=3)=[C:11]3[NH:12][CH2:13][CH2:14][CH2:15][N:10]3[N:9]=2)=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 1355153842-(4-Fluorophenyl)-3-(pyridin-4-yl)-4,5,6,7-tetrahydropyrazolo[1,5-a]pyrimidine

Product 1

HCID 1363784182-(4-Fluorophenyl)-3-(pyridin-4-yl)-4,5,6,7-tetrahydropyrazolo[1,5-a]pyrimidine hydrochloride

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a suspension of 2-(4-fluorophenyl)-3-(pyridin-4-yl)-4,5,6,7-tetrahydropyrazolo[1,5-a]pyrimidine (250 mg) in ethanol (3.5 ml) was added 1N hydrochloric acid (0.85 ml). The resulting clear solution was concentrated in vacuo. To the residue was added ethanol (1 ml) and the solution was concentrated in vacuo. The residue was crystallized from a mixture of methanol (0.5 ml) and ethyl acetate (3 ml) and recrystallized from an aqueous isopropyl alcohol solution to give 2-(4-fluorophenyl)-3-(pyridin-4-yl)-4,5,6,7-tetrahydropyrazolo[1,5-a]pyrimidine hydrochloride (233 mg).

Workup

  1. concentrationThe resulting clear solution was concentrated in vacuo
  2. additionTo the residue was added ethanol (1 ml)
  3. concentrationthe solution was concentrated in vacuo
  4. customThe residue was crystallized from a mixture of methanol (0.5 ml) and ethyl acetate (3 ml)
  5. customrecrystallized from an aqueous isopropyl alcohol solution

Sources & evidence

ORD record
ord-2bf86c20845747d0b497d8ed708c9cd8
Source dataset
uspto-grants-1997_04
Patent number
US05624931

Reaction notes

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