Ethyl Acetoacetate → HCID 178429158, compound

HRID 928249Notes

Reaction equation

HRID 928249 reaction equation
[C:1]1([C:7]2[NH:11][N:10]=[C:9]([NH2:12])[CH:8]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C([O:15][C:16](=O)[CH2:17][C:18](=O)[CH3:19])C>C1(C)C=CC=CC=1>[CH3:19][C:18]1[NH:12][C:9]2[N:10]([N:11]=[C:7]([C:1]3[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=3)[CH:8]=2)[C:16](=[O:15])[CH:17]=1

Participants

4

Reactant 2

HCID 8868Ethyl AcetoacetateHCID 1366553-Amino-5-phenylpyrazole

Product 1

HCID 178429158HCID 178429158, compoundYield 81.3%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
120 °C

Procedure

A mixture of 5-phenyl-1H-pyrazol-3-ylamine (501 mg, 3.15 mmol) and 3-oxobutanoic acid ethyl ester (0.433 mL, 3.39 mmol) in anhydrous toluene (2.9 mL) is heated at 120° C. in a sealed vial. After 2 hr, the reaction is cooled to room temperature. The precipitate is collected in a Buchner funnel and washed with hexanes to afford 5-methyl-2-phenylpyrazolo[1,5-a]pyrimidin-7(4H)-one (577 mg, yield 81%). LCMS: (AA) M+1 226; 1H NMR (400 MHz, DMSO) δ 12.35 (s, 1H), 8.01-7.92 (m, 2H), 7.49-7.43 (m, 2H), 7.42-7.37 (m, 1H), 6.57 (s, 1H), 5.60 (s, 1H), 2.29 (s, 3H).

Workup

  1. temperaturethe reaction is cooled to room temperature
  2. customThe precipitate is collected in a Buchner funnel
  3. washwashed with hexanes

Sources & evidence

ORD record
ord-3e4b30f5db3c4472a36b1ce16f3d903b
Source dataset
uspto-grants-2016_03
Patent number
US09290500B2

Reaction notes

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