Ammonia → 1,5-Diphenylpyrazolo[1,5-a]pyrimidin-7(1H)-one

HRID 2071646Notes

Reaction equation

HRID 2071646 reaction equation
[NH2:1][C:2]1[CH:3]=[CH:4][N:5]([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=2)[N:6]=1.C([O:15][C:16](=O)[CH2:17][C:18](=O)[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)C.N>O>[C:7]1([N:5]2[N:6]3[C:16](=[O:15])[CH:17]=[C:18]([C:19]4[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=4)[N:1]=[C:2]3[CH:3]=[CH:4]2)[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1

Participants

5

Reactant 3

HCID 222AmmoniaHCID 7170Ethyl benzoylacetateHCID 5943201-phenyl-1H-pyrazol-3-amine

Product 1

HCID 133591001,5-Diphenylpyrazolo[1,5-a]pyrimidin-7(1H)-one

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 10 g. of 5-amino-2-phenylpyrazole (0.063 mol.), 12.1 g. of benzoylacetic acid ethyl ester (0.063 mol.) and 50 g. of polyphosphoric acid is heated at 110°-120° with stirring for 90 minutes. After cooling, 200 ml. of water and then concentrated aqueous ammonia is added under external cooling to adjust the mixture to pH 9. The collected 1,5-diphenylpyrazolo[1,5-a]pyrimidin-7(1H)-one is washed with water and dried at 70°, yield: 17 g. (94%); m.p. 194°-200°. A sample, recrystallized from absolute ethanol, melts at 205°-207°.

Workup

  1. additionA mixture of 10 g
  2. temperatureAfter cooling
  3. temperatureunder external cooling
  4. washThe collected 1,5-diphenylpyrazolo[1,5-a]pyrimidin-7(1H)-one is washed with water
  5. customdried at 70°
  6. customA sample, recrystallized from absolute ethanol, melts at 205°-207°

Sources & evidence

ORD record
ord-fccd25a2cfa345ddbcc281d204fab5ea
Source dataset
uspto-grants-1977_09
Patent number
US04048184

Reaction notes

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