Ethyl benzoylacetate → HCID 178469958, compound

HRID 386648

Reaction equation

HRID 386648 reaction equation
[NH2:1][C:2]1[NH:6][N:5]=[CH:4][C:3]=1[C:7]([O:9][CH2:10][CH3:11])=[O:8].O=[C:13]([C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)[CH2:14][C:15](OCC)=[O:16]>C(O)(=O)C>[OH:16][C:15]1[N:6]2[N:5]=[CH:4][C:3]([C:7]([O:9][CH2:10][CH3:11])=[O:8])=[C:2]2[N:1]=[C:13]([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[CH:14]=1

Participants

4

Reactant 2

HCID 7170Ethyl benzoylacetateHCID 81472ethyl 3-amino-1H-pyrazole-4-carboxylate

Product 1

HCID 178469958HCID 178469958, compoundYield 61%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

Commercially available ethyl 5-amino-1H-pyrazole-4-carboxylate (5.0 g, 32 mmol) was taken into glacial acetic acid (3.2 mL) followed by addition of ethyl 3-oxo-3-phenylpropanoate (6.1 mL, 35 mmol) and the mixture was refluxed for 12 h. The mixture was allowed to cool to room temperature and concentrated in vacuo. The crude solid was recrystallized (ethanol) and collected to yield 3.1 g (61%) of crystalline ethyl 7-hydroxy-5-phenylpyrazolo[1,5-a]pyrimidine-3-carboxylate. 1H NMR (400 MHz, d6-DMSO): 11.75 (s, 1H), 8.28 (s, 1H), 7.80 (m, 2H), 7.61 (m, 3H), 6.28 (s, 1H), 4.31 (q, 2H), 1.34 (t, 3H).

Workup

  1. temperaturethe mixture was refluxed for 12 h
  2. concentrationconcentrated in vacuo
  3. customThe crude solid was recrystallized (ethanol)
  4. customcollected

Sources & evidence

ORD record
ord-d0ac4a62de4d465aa9805715d06346f8
Source dataset
uspto-grants-2013_02
Patent number
US08372851B2

Linked notes

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