Ethyl Acetate → HCID 178469959, compound

HRID 1801751Notes

Reaction equation

HRID 1801751 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8](=O)[CH2:9][C:10]([O:12]CC)=O)=[CH:4][CH:3]=1.[NH2:16][C:17]1[NH:21][N:20]=[CH:19][C:18]=1[C:22]([O:24][CH2:25][CH3:26])=[O:23].C(OCC)(=O)C>CCCCCC>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[CH:9]=[C:10]([OH:12])[N:21]3[N:20]=[CH:19][C:18]([C:22]([O:24][CH2:25][CH3:26])=[O:23])=[C:17]3[N:16]=2)=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 8857Ethyl AcetateHCID 81472ethyl 3-amino-1H-pyrazole-4-carboxylateHCID 101336Ethyl 3-(4-chlorophenyl)-3-oxopropanoate

Product 1

HCID 178469959HCID 178469959, compoundYield 52.3%

Reagents, catalysts & solvents 1

HCID 8058HexaneSolvent

Conditions

Temperature
160 °C

Procedure

A mixture of ethyl 3-(4-chloro-phenyl)-3-oxo-propionate (18.1 g, 0.080 mol) and ethyl 5-amino-1H-pyrazole-4-carboxylate (13.7 g, 0.088 mol) was stirred at for 3 h 160° C. Ethyl acetate (40 mL) and hexane (40 mL) were successively added to the cooled mixture and stirring was continued at 0° C. for 0.5 h. The crystals were isolated by filtration and triturated for 1.2 h with 0.2 N HCl (80 mL). The solid was filtered off, washed with water and dried to give ethyl 5-(4-chloro-phenyl)-7-hydroxy-pyrazolo[1,5-a]pyrimidine-3-carboxylate (13.3 g, 52%). White solid. MS (ISN) 316.3 [(M−H)−]; mp 190-192° C.

Workup

  1. stirringstirring
  2. waitwas continued at 0° C. for 0.5 h
  3. customThe crystals were isolated by filtration
  4. customtriturated for 1.2 h with 0.2 N HCl (80 mL)
  5. filtrationThe solid was filtered off
  6. washwashed with water
  7. customdried

Sources & evidence

ORD record
ord-4f3b51f8bc1b4a6daff8c0e54bdda382
Source dataset
uspto-grants-2013_01
Patent number
US08349844B2

Reaction notes

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