Water → HCID 22249906, compound

HRID 966027Notes

Reaction equation

HRID 966027 reaction equation
[Cl:1][C:2]1[N:7]2[N:8]=[C:9]([CH3:20])[C:10]([C:11]3[C:16]([CH3:17])=[CH:15][C:14]([CH3:18])=[CH:13][C:12]=3[CH3:19])=[C:6]2[N:5]=[C:4]([CH3:21])[C:3]=1[CH2:22][CH2:23]Cl.[NH2:25][CH:26]([CH2:29][CH3:30])[CH2:27][CH3:28].O.C(OCC)(=O)C>C(C(C)=O)C>[ClH:1].[CH2:27]([CH:26]([N:25]1[C:2]2[N:7]3[N:8]=[C:9]([CH3:20])[C:10]([C:11]4[C:16]([CH3:17])=[CH:15][C:14]([CH3:18])=[CH:13][C:12]=4[CH3:19])=[C:6]3[N:5]=[C:4]([CH3:21])[C:3]=2[CH2:22][CH2:23]1)[CH2:29][CH3:30])[CH3:28]

Participants

6

Reactant 4

HCID 962WaterHCID 8857Ethyl AcetateHCID 120193-Pentanamine2×HCID 22249724HCID 22249724, compound

Product 1

HCID 22249906HCID 22249906, compound

Reagents, catalysts & solvents 1

HCID 6569Methyl Ethyl KetoneSolvent

Procedure

A solution of 7-chloro-6-(2-chloroethyl)-3-mesityl-2,5-dimethylpyrazolo[1,5-a]pyrimidine (1.5 g, 4.14 mmol) and 3-aminopentane (3 mL) in methyl ethyl ketone (15 mL) was heated under reflux for one hour. 3-Aminopentane (6 mL) was added thereto, followed by heating under reflux for further 4.5 hours. Water was added to the reaction mixture, followed by extcarting with ethyl acetate, The organic layer was washed with brine, dried over anhydrous magnesium sulfate and evaporated. The residue was purified by silica gel column chromatography (10-50% ethyl acetate/hexane), to give the title compound (1.02 g) as a pale yellow oil.

Workup

  1. temperatureunder reflux for one hour
  2. temperatureby heating
  3. temperatureunder reflux for further 4.5 hours
  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 (10-50% ethyl acetate/hexane)

Sources & evidence

ORD record
ord-b9fdb71a7ebe464192c853f9ac0646d1
Source dataset
uspto-grants-2005_10
Patent number
US06951865B2

Reaction notes

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