2,4-Nonanedione → 7-Butyl-2,5-dimethyl-pyrazolo[1,5-a]pyrimidine

HRID 1639654Notes

Reaction equation

HRID 1639654 reaction equation
[CH3:1][C:2]1[CH:3]=[C:4]([NH2:7])[NH:5][N:6]=1.[CH3:8][C:9](=O)[CH2:10][C:11](=O)[CH2:12][CH2:13][CH2:14][CH2:15]C>N1CCCCC1.C(O)C>[CH2:12]([C:11]1[N:5]2[N:6]=[C:2]([CH3:1])[CH:3]=[C:4]2[N:7]=[C:9]([CH3:8])[CH:10]=1)[CH2:13][CH2:14][CH3:15]

Participants

5

Reactant 2

HCID 803142,4-NonanedioneHCID 178418690HCID 178418690, compound

Product 1

HCID 248985227-Butyl-2,5-dimethyl-pyrazolo[1,5-a]pyrimidine

Reagents, catalysts & solvents 2

HCID 8082PiperidineCatalystHCID 702EthanolSolvent

Conditions

Temperature
80 °C

Procedure

Add 5-methyl-2H-pyrazol-3-ylamine (217 mg, 2.17 mmol), nonane-2,4-dione (339 mg, 2.39 mmol) and piperidine (1 drop) to ethanol (10 mL) and heat at 80° C. overnight. Cool to room temperature and concentrate to dryness. Purify by silica gel column chromatography (0-20% ethyl acetate in hexane) to obtain a mixture of two isomers (2 g).

Workup

  1. temperatureCool to room temperature
  2. concentrationconcentrate to dryness
  3. customPurify by silica gel column chromatography (0-20% ethyl acetate in hexane)
  4. customto obtain
  5. additiona mixture of two isomers (2 g)

Sources & evidence

ORD record
ord-df1d26e776d6488992ecdc1229536c12
Source dataset
uspto-grants-2012_02
Patent number
US08110580B2

Reaction notes

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