Potassium Carbonate → 3-(1-(4-Amino-1H-pyrazolo[3,4-d]pyrimidin-1-yl)ethyl)-4-phenyl-1H-isochromen-1-one

HRID 634446Notes

Reaction equation

HRID 634446 reaction equation
Br[CH:2]([C:4]1[O:5][C:6](=[O:20])[C:7]2[C:12]([C:13]=1[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)=[CH:11][CH:10]=[CH:9][CH:8]=2)[CH3:3].[NH:21]1[C:25]2=[N:26][CH:27]=[N:28][C:29]([NH2:30])=[C:24]2[CH:23]=[N:22]1.C([O-])([O-])=O.[K+].[K+]>CN(C=O)C>[NH2:30][C:29]1[N:28]=[CH:27][N:26]=[C:25]2[N:21]([CH:2]([C:4]3[O:5][C:6](=[O:20])[C:7]4[C:12]([C:13]=3[C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=3)=[CH:11][CH:10]=[CH:9][CH:8]=4)[CH3:3])[N:22]=[CH:23][C:24]=12

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 754201H-Pyrazolo[3,4-d]pyrimidin-4-amineHCID 1181310753-(1-Bromoethyl)-4-phenyl-1H-isochromen-1-one2×

Product 1

HCID 1181311313-(1-(4-Amino-1H-pyrazolo[3,4-d]pyrimidin-1-yl)ethyl)-4-phenyl-1H-isochromen-1-oneYield 34.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

The title compound was made in a similar way as that of the compound of example 15, 3-(1-bromoethyl)-4-phenyl-1H-isochromen-1-one (intermediate C7, 70 mg, 0.213 mmol), 1H-pyrazolo[3,4-d]pyrimidin-4-amine (40.2 mg, 0.298 mmol) and K2CO3 (41.1 mg, 0.298 mmol) in DMF (1 ml) at 80° C. for 4 hrs to give the title compound (28 mg, 34%).

Workup

  1. customat 80° C.
  2. customfor 4 hrs

Sources & evidence

ORD record
ord-e4329b0c6e644889bdfb37706a4adc78
Source dataset
uspto-grants-2016_04
Patent number
US09321776B2

Reaction notes

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