3-Amino-5-phenylpyrazole → HCID 178432076, compound

HRID 1896418Notes

Reaction equation

HRID 1896418 reaction equation
[C:1]1([C:7]2[CH:11]=[C:10]([NH2:12])[NH:9][N:8]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[F:13][CH:14]([C:20](=O)[CH3:21])[C:15](OCC)=[O:16]>CC(O)=O>[F:13][C:14]1[C:20]([CH3:21])=[N:12][C:10]2[N:9]([N:8]=[C:7]([C:1]3[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=3)[CH:11]=2)[C:15]=1[OH:16]

Participants

4

Reactant 2

HCID 1366553-Amino-5-phenylpyrazoleHCID 230078Ethyl 2-fluoroacetoacetate

Product 1

HCID 178432076HCID 178432076, compoundYield 64%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Conditions

Temperature
100 °C

Procedure

To a solution of 3-phenyl-1H-pyrazol-5-amine x131 (52 mmol, 1 eq, 8.3 g) in 50 ml of AcOH, is added ethyl 2-fluoro-3-oxobutanoate x132 (57 mmol, 1.2 eq, 8.5 g). The mixture is heated at 100° C. for 0.5 hour. After cooling to room temperature, the resulting product is filtered, washed with EtOH and dried to afford 8.1 g of 6-fluoro-5-methyl-2-phenylpyrazolo[1,5-a]pyrimidin-7-ol x133.

Workup

  1. temperatureAfter cooling to room temperature
  2. filtrationthe resulting product is filtered
  3. washwashed with EtOH
  4. customdried

Sources & evidence

ORD record
ord-1b8b0ee47a32472293815c0dc8fef115
Source dataset
uspto-grants-2013_08
Patent number
US08518943B2

Reaction notes

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