3-Pentanamine → Ethyl 7-[(1-ethylpropyl)amino]-3-mesityl-2,5-dimethylpyrazolo[1,5-a]pyrimidine-6-carboxylate

HRID 966038Notes

Reaction equation

HRID 966038 reaction equation
[NH2:1][CH:2]([CH2:5][CH3:6])[CH2:3][CH3:4].Cl[C:8]1[N:13]2[N:14]=[C:15]([CH3:26])[C:16]([C:17]3[C:22]([CH3:23])=[CH:21][C:20]([CH3:24])=[CH:19][C:18]=3[CH3:25])=[C:12]2[N:11]=[C:10]([CH3:27])[C:9]=1[C:28]([O:30][CH2:31][CH3:32])=[O:29]>C(#N)C>[CH2:3]([CH:2]([NH:1][C:8]1[N:13]2[N:14]=[C:15]([CH3:26])[C:16]([C:17]3[C:22]([CH3:23])=[CH:21][C:20]([CH3:24])=[CH:19][C:18]=3[CH3:25])=[C:12]2[N:11]=[C:10]([CH3:27])[C:9]=1[C:28]([O:30][CH2:31][CH3:32])=[O:29])[CH2:5][CH3:6])[CH3:4]

Participants

4

Reactant 2

HCID 120193-PentanamineHCID 22249592Ethyl 7-chloro-3mesityl-2,5-dimethylpyrazolo[1,5-a]pyrimidin-6-carboxylate

Product 1

HCID 22249551Ethyl 7-[(1-ethylpropyl)amino]-3-mesityl-2,5-dimethylpyrazolo[1,5-a]pyrimidine-6-carboxylate

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

3-Aminopentane (5 mL) was added to a solution of ethyl 7-chloro-3-mesityl-2,5-dimethylpyrazolo[1,5-a]pyrimidin-6-carboxylate (1.94 g, 5.22 mmol) in acetonitrile (20 mL), followed by heating under reflux for eight hours. The mixture was extracted with ethyl acetate, and the organic layer was washed with brine, dried over anhydrous magnesium sulfate and evaporated. The residue was purified by silica gel column chromatography (20% ethyl acetate/hexane), to give the title compound (1.70 g).

Workup

  1. temperatureby heating
  2. temperatureunder reflux for eight hours
  3. extractionThe mixture was extracted with ethyl acetate
  4. washthe organic layer was washed with brine
  5. dry with materialdried over anhydrous magnesium sulfate
  6. customevaporated
  7. customThe residue was purified by silica gel column chromatography (20% ethyl acetate/hexane)

Sources & evidence

ORD record
ord-0f17c96e9a3b44029dce3fa2d059cbb9
Source dataset
uspto-grants-2005_10
Patent number
US06951865B2

Reaction notes

Loading…