N-[(2,5-Dimethylphenyl)methyl]cyclopentanamine → 4-[N-(2,5-Dimethylbenzyl)-cyclopentylamino]-1-(tetrahydrofuran-2-yl)-1H-pyrazolo[3,4-d]pyrimidine

HRID 1199962Notes

Reaction equation

HRID 1199962 reaction equation
Cl[C:2]1[N:7]=[CH:6][N:5]=[C:4]2[N:8]([CH:11]3[CH2:15][CH2:14][CH2:13][O:12]3)[N:9]=[CH:10][C:3]=12.[CH3:16][C:17]1[CH:29]=[CH:28][C:27]([CH3:30])=[CH:26][C:18]=1[CH2:19][NH:20][CH:21]1[CH2:25][CH2:24][CH2:23][CH2:22]1>C(O)CCC>[CH3:16][C:17]1[CH:29]=[CH:28][C:27]([CH3:30])=[CH:26][C:18]=1[CH2:19][N:20]([CH:21]1[CH2:25][CH2:24][CH2:23][CH2:22]1)[C:2]1[N:7]=[CH:6][N:5]=[C:4]2[N:8]([CH:11]3[CH2:15][CH2:14][CH2:13][O:12]3)[N:9]=[CH:10][C:3]=12

Participants

4

Reactant 2

HCID 19864492N-[(2,5-Dimethylphenyl)methyl]cyclopentanamineHCID 198644974-chloro-1-(tetrahydrofuran-2-yl)-1H-pyrazolo[3,4-d]pyrimidine

Product 1

HCID 142567954-[N-(2,5-Dimethylbenzyl)-cyclopentylamino]-1-(tetrahydrofuran-2-yl)-1H-pyrazolo[3,4-d]pyrimidine

Reagents, catalysts & solvents 1

HCID 2631-ButanolSolvent

Procedure

A mixture of 7.8 g. (35 mmole) 4-chloro-1-(tetrahydrofuran-2-yl)-1H-pyrazolo[3,4-d]pyrimidine, 20.3 g. (100 mmole) N-(2,5-dimethylbenzyl)-cyclopentylamine and 100 ml. n-butanol is heated under reflux for 16 hours. The reaction mixture is evaporated, the residue is taken up in water and extracted with dichloromethane and the extract is washed with dilute acetic acid and dilute aqueous sodium hydrogen carbonate solution, dried, evaporated and chromatographed on silica gel. 5.0 g. (37% of theory) of the title compound are eluted with dichloromethane/methanol (98:2 v/v) which, after trituration with diethyl ether, melts at 173°-174° C.

Workup

  1. additionA mixture of 7.8 g
  2. temperatureunder reflux for 16 hours
  3. customThe reaction mixture is evaporated
  4. extractionextracted with dichloromethane
  5. washthe extract is washed with dilute acetic acid and dilute aqueous sodium hydrogen carbonate solution
  6. customdried
  7. customevaporated
  8. customchromatographed on silica gel
  9. wash(37% of theory) of the title compound are eluted with dichloromethane/methanol (98:2 v/v) which

Sources & evidence

ORD record
ord-1e7cf1b1030f4081aa10a58f1844d85a
Source dataset
uspto-grants-1990_02
Patent number
US04904666

Reaction notes

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