1,3-Diethyl 2-acetylpropanedioate → HCID 178469172, compound

HRID 1393656Notes

Reaction equation

HRID 1393656 reaction equation
[NH2:1][C:2]1[CH:6]=[C:5]([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=2)[NH:4][N:3]=1.[CH3:13][CH2:14][O:15][C:16]([CH:18]([C:22](OCC)=[O:23])[C:19]([CH3:21])=O)=[O:17]>C(O)(=O)C>[OH:23][C:22]1[N:3]2[N:4]=[C:5]([C:7]3[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=3)[CH:6]=[C:2]2[N:1]=[C:19]([CH3:21])[C:18]=1[C:16]([O:15][CH2:14][CH3:13])=[O:17]

Participants

4

Reactant 2

HCID 1363651,3-Diethyl 2-acetylpropanedioateHCID 1366553-Amino-5-phenylpyrazole

Product 1

HCID 178469172HCID 178469172, compoundYield 93,700.203%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Conditions

Temperature
120 °C

Procedure

3-Amino-5-phenylpyrazole (1.56 mg) and diethyl acetomalonate (2.00 g) were dissolved in acetic acid (5.0 ml) and stirred for 3 hours at 120° C. The reaction mixture was cooled to room temperature and concentrated under reduced pressure. Ethanol was added to the residue which were then cooled to 0° C. Precipitated crystals were collected by filtration and washed with cold ethanol. The crystals were dried under reduced pressure to give ethyl 7-hydroxy-5-methyl-2-phenylpyrazolo[1,5-a]pyrimidine-6-carboxylate (2.73 g, Y.:92%) as white crystals.

Workup

  1. temperatureThe reaction mixture was cooled to room temperature
  2. concentrationconcentrated under reduced pressure
  3. additionEthanol was added to the residue which
  4. temperaturewere then cooled to 0° C
  5. customPrecipitated crystals
  6. filtrationwere collected by filtration
  7. washwashed with cold ethanol
  8. customThe crystals were dried under reduced pressure

Sources & evidence

ORD record
ord-4fad178cdc6f4f5bbe648b473bef7a37
Source dataset
uspto-grants-2008_03
Patent number
US07345180B2

Reaction notes

Loading…