Methyl 3-oxoheptanoate → HCID 178441198, compound

HRID 1455997Notes

Reaction equation

HRID 1455997 reaction equation
[NH2:1][C:2]1[CH:6]=[CH:5][NH:4][N:3]=1.O=[C:8]([CH2:14][CH2:15][CH2:16][CH3:17])[CH2:9][C:10](OC)=[O:11]>C1(C)C=CC=CC=1>[CH2:14]([C:8]1[CH:9]=[C:10]([OH:11])[N:3]2[N:4]=[CH:5][CH:6]=[C:2]2[N:1]=1)[CH2:15][CH2:16][CH3:17]

Participants

4

Reactant 2

HCID 546075Methyl 3-oxoheptanoateHCID 178418806HCID 178418806, compound

Product 1

HCID 178441198HCID 178441198, compoundYield 80.1%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
100 °C

Procedure

A suspension of 100 g of 3-aminopyrazole and 190 g of methyl 3-oxoheptanoate in 120 ml of toluene was heated under reflux at 100° C. for 3 hours and cooled. Toluene was distilled off under reduced pressure, and diethyl ether was added to the residue. The crystals precipitated were collected and sequentially washed with diethyl ether and acetonitrile to provide 184 g of 5-n-butyl-7-hydroxypyrazolo[1,5-a]pyrimidine as colorless crystals. The structure and melting point of the compound obtained are shown in Table 1 below.

Workup

  1. temperaturewas heated
  2. temperaturecooled
  3. distillationToluene was distilled off under reduced pressure, and diethyl ether
  4. additionwas added to the residue
  5. customThe crystals precipitated
  6. customwere collected
  7. washsequentially washed with diethyl ether and acetonitrile

Sources & evidence

ORD record
ord-752420e2becf4e538d295bc827adb042
Source dataset
uspto-grants-1998_12
Patent number
US05843951

Reaction notes

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