Diisopropylethylamine → 4-((3-(3-Chlorophenyl)pyrazolo[1,5-a]pyrimidin-5-yl)amino)cyclohexanone

HRID 1483857Notes

Reaction equation

HRID 1483857 reaction equation
Cl[C:2]1[CH:7]=[CH:6][N:5]2[N:8]=[CH:9][C:10]([C:11]3[CH:16]=[CH:15][CH:14]=[C:13]([Cl:17])[CH:12]=3)=[C:4]2[N:3]=1.[NH2:18][CH:19]1[CH2:24][CH2:23][C:22](=[O:25])[CH2:21][CH2:20]1.CCN(C(C)C)C(C)C>CC(O)C.C([O-])(O)=O.[Na+]>[Cl:17][C:13]1[CH:12]=[C:11]([C:10]2[CH:9]=[N:8][N:5]3[CH:6]=[CH:7][C:2]([NH:18][CH:19]4[CH2:24][CH2:23][C:22](=[O:25])[CH2:21][CH2:20]4)=[N:3][C:4]=23)[CH:16]=[CH:15][CH:14]=1

Participants

6

Reactant 3

HCID 81531DiisopropylethylamineHCID 99123064-AminocyclohexanoneHCID 596622385-Chloro-3-(3-chloro-phenyl)-pyrazolo[1,5-a]pyrimidine

Product 1

HCID 712276764-((3-(3-Chlorophenyl)pyrazolo[1,5-a]pyrimidin-5-yl)amino)cyclohexanoneYield 24%

Reagents, catalysts & solvents 2

HCID 3776IsopropanolSolventHCID 516892Sodium BicarbonateSolvent

Procedure

A mixture of 5-chloro-3-(3-chlorophenyl)pyrazolo[1,5-a]pyrimidine (100 mg, 0.379 mmol), 4-aminocyclohexanone (43 mg, 0.379 mmol), and DIEA (0.158 ml, 1.515 mmol) in 2-propanol (3 ml) was irradiated to 150° C. for 14 h in a Biotage microwave. After cooling, the mixture was diluted with saturated aqueous NaHCO3, and extracted three times with EtOAc. The combined extracts were washed with brine, dried over Na2SO4 and concentrated in vacuo. After absorbing on celite, the compound was purified by chromatography (12 g silica, 0-15% methanol/DCM) to give 4-((3-(3-chlorophenyl)pyrazolo[1,5-a]pyrimidin-5-yl)amino)cyclohexanone (30 mg, 24% yield) as a white solid.

Workup

  1. customwas irradiated to 150° C. for 14 h in a Biotage microwave
  2. temperatureAfter cooling
  3. extractionextracted three times with EtOAc
  4. washThe combined extracts were washed with brine
  5. dry with materialdried over Na2SO4
  6. concentrationconcentrated in vacuo
  7. customAfter absorbing on celite
  8. customthe compound was purified by chromatography (12 g silica, 0-15% methanol/DCM)

Sources & evidence

ORD record
ord-ff6934fe1d084306b90b6ee2335a8a89
Source dataset
uspto-grants-2016_08
Patent number
US09416132B2

Reaction notes

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