Water → Ethyl 2-[7-[(1-Ethylpropyl)amino]-3-mesityl-2,5-dimethylpyrazolo[1,5-a]pyrimidin-6-yl]acetate

HRID 965991Notes

Reaction equation

HRID 965991 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[CH2:28][C:29]([O:31][CH2:32][CH3:33])=[O:30].O>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[CH2:28][C:29]([O:31][CH2:32][CH3:33])=[O:30])[CH2:5][CH3:6])[CH3:4]

Participants

5

Reactant 3

HCID 962WaterHCID 120193-PentanamineHCID 22249832Ethyl 2-(7-chloro-3-mesityl-2,5-dimethylpyrazolo[1,5-a]pyrimidin-6-yl)acetate

Product 1

HCID 22249510Ethyl 2-[7-[(1-Ethylpropyl)amino]-3-mesityl-2,5-dimethylpyrazolo[1,5-a]pyrimidin-6-yl]acetate

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

3-Aminopentane (0.6 mL) was added to a solution of ethyl 2-(7-chloro-3-mesityl-2,5-dimethylpyrazolo[1,5-a]pyrimidin-6-yl)acetate (130 mg) in acetonitrile (5 mL), followed by heating under reflux overnight. After cooling the reaction solution, water was added thereto. The mixture was extracted twice with ethylacetate, and the organic layer was washed with an aqueus saturated solution of sodium bicarbonate, and then dried over anhydrous magnesium sulfate. The solvent was evaporated, and the residue was purified by silica gel column chromatography, to give the title compound (84 mg) as a green oil.

Workup

  1. temperatureby heating
  2. temperatureunder reflux overnight
  3. additionwas added
  4. extractionThe mixture was extracted twice with ethylacetate
  5. washthe organic layer was washed with an aqueus saturated solution of sodium bicarbonate
  6. dry with materialdried over anhydrous magnesium sulfate
  7. customThe solvent was evaporated
  8. customthe residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-98e2650b27ce47e7b977fa1ed8f64861
Source dataset
uspto-grants-2005_10
Patent number
US06951865B2

Reaction notes

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