Triethylamine → HCID 178437862, compound

HRID 1736587Notes

Reaction equation

HRID 1736587 reaction equation
[CH:1]1([N:6]2[C:10]3=[N:11][C:12]([C:16]4[CH:21]=[C:20]([CH3:22])[N:19]=[C:18](Cl)[CH:17]=4)=[N:13][C:14](=[O:15])[C:9]3=[C:8]([CH2:24][CH3:25])[NH:7]2)[CH2:5][CH2:4][CH2:3][CH2:2]1.C(N(CC)CC)C>[Pd].CN(C=O)C>[CH:1]1([N:6]2[C:10]3=[N:11][C:12]([C:16]4[CH:17]=[CH:18][N:19]=[C:20]([CH3:22])[CH:21]=4)=[N:13][C:14](=[O:15])[C:9]3=[C:8]([CH2:24][CH3:25])[NH:7]2)[CH2:2][CH2:3][CH2:4][CH2:5]1

Participants

5

Reactant 2

HCID 8471TriethylamineHCID 178437852HCID 178437852, compound

Product 1

HCID 178437862HCID 178437862, compoundYield 82.5%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 6228DimethylformamideSolvent

Conditions

Temperature
60 °C

Procedure

A mixture of 1-cyclopentyl-3-ethyl-6-(2-chloro-6-methyl-4-pyridyl)pyrazolo[3,4-d]pyrimidin-4-one (1.3 g, 3.6 mmol), DMF (75 ml), triethylamine (1.0 ml, 7.2 mmol) and 10% palladium on carbon (0.13 g) was placed on a parr hydrogenator at 50 psi and heated via an external heating jacket to 60° C. for 2 hours, then at 70° C. for 6.5 hours. Additional catalyst was added and the mixture was placed back on the parr hydrogenator for 4 hours at 70° C. The mixture was filtered through a celite plug while hot, and the filtrate was concentrated in vacuo. Water was added to the residue and a white solid was collected by filtration to afford 0.96 g (82%) of 1-cyclopentyl-3-ethyl-6-(2-methyl-4-pyridyl)pyrazolo[3,4-d]pyrimidin-4-one as a white powder, m.p. 258°-259° C. when recrystallized from DMF/acetonitrile.

Workup

  1. additionAdditional catalyst was added
  2. waitthe mixture was placed back on the parr hydrogenator for 4 hours at 70° C
  3. filtrationThe mixture was filtered through a celite plug while hot, and the filtrate
  4. concentrationwas concentrated in vacuo
  5. additionWater was added to the residue
  6. filtrationa white solid was collected by filtration

Sources & evidence

ORD record
ord-3c8933a3304c4b94b114b861e15b9098
Source dataset
uspto-grants-1996_07
Patent number
US05541187

Reaction notes

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