Water → HCID 22249906, compound

HRID 584818Notes

Reaction equation

HRID 584818 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-de417b74fd834c8989b1002541fce5a0
Source dataset
uspto-grants-2005_08
Patent number
US06927221B2

Reaction notes

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