Hydrochloric Acid → HCID 178516614, compound

HRID 54957Notes

Reaction equation

HRID 54957 reaction equation
[Na].[NH2:2][C:3]1[NH:7][N:6]=[C:5]([C:8]2[CH:13]=[CH:12][C:11]([F:14])=[CH:10][CH:9]=2)[C:4]=1[C:15]1[CH:20]=[CH:19][N:18]=[CH:17][CH:16]=1.[C:21](OCC)(=[O:28])[CH2:22][C:23](OCC)=[O:24].Cl>C(O)C.O>[OH:24][C:23]1[CH:22]=[C:21]([OH:28])[N:7]2[N:6]=[C:5]([C:8]3[CH:13]=[CH:12][C:11]([F:14])=[CH:10][CH:9]=3)[C:4]([C:15]3[CH:20]=[CH:19][N:18]=[CH:17][CH:16]=3)=[C:3]2[N:2]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 7761Diethyl MalonateHCID 5360545SodiumHCID 178509109HCID 178509109, compound

Product 1

HCID 178516614HCID 178516614, compoundYield 65.2%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

To a solution of sodium (51 mg) in dry ethanol (3 ml) was added 5-amino-3-(4-fluorophenyl)-4-(pyridin-4-yl)pyrazole (254 mg) and diethyl malonate (176 mg). The mixture was refluxed for 5 hours and cooled. To the reaction mixture were added 1N-hydrochloric acid (4 ml) and water (6 ml). The separated solid was collected, washed with water and dried to give 5,7-dihydroxy-2-(4-fluorophenyl)-3-(pyridin-4-yl)pyrazolo[1,5-a]pyrimidine (210 mg).

Workup

  1. temperatureThe mixture was refluxed for 5 hours
  2. temperaturecooled
  3. customThe separated solid was collected
  4. washwashed with water
  5. customdried

Sources & evidence

ORD record
ord-1a25ebf0224649d194510381979efe57
Source dataset
uspto-grants-1997_04
Patent number
US05624931

Reaction notes

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