Potassium Carbonate → 3-(1-(4-Amino-1H-pyrazolo[3,4-d]pyrimidin-1-yl)ethyl)-4-(thiazol-5-yl)-1H-isochromen-1-one

HRID 634447Notes

Reaction equation

HRID 634447 reaction equation
Br[CH:2]([C:4]1[O:5][C:6](=[O:19])[C:7]2[C:12]([C:13]=1[C:14]1[S:18][CH:17]=[N:16][CH:15]=1)=[CH:11][CH:10]=[CH:9][CH:8]=2)[CH3:3].[NH:20]1[C:24]2=[N:25][CH:26]=[N:27][C:28]([NH2:29])=[C:23]2[CH:22]=[N:21]1.C([O-])([O-])=O.[K+].[K+]>CN(C=O)C>[NH2:29][C:28]1[N:27]=[CH:26][N:25]=[C:24]2[N:20]([CH:2]([C:4]3[O:5][C:6](=[O:19])[C:7]4[C:12]([C:13]=3[C:14]3[S:18][CH:17]=[N:16][CH:15]=3)=[CH:11][CH:10]=[CH:9][CH:8]=4)[CH3:3])[N:21]=[CH:22][C:23]=12

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 754201H-Pyrazolo[3,4-d]pyrimidin-4-amineHCID 1181310683-(1-Bromoethyl)-4-(thiazol-5-yl)-1H-isochromen-1-one

Product 1

HCID 1181313283-(1-(4-Amino-1H-pyrazolo[3,4-d]pyrimidin-1-yl)ethyl)-4-(thiazol-5-yl)-1H-isochromen-1-oneYield 54%

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-(thiazol-5-yl)-1H-isochromen-1-one (intermediate C12, 56 mg, 0.17 mmol), 1H-pyrazolo[3,4-d]pyrimidin-4-amine (45 mg, 0.33 mmol) and K2CO3 (46 mg, 0.33 mmol) in DMF (1 ml) at 80° C. for 3 hrs to give the title compound (35 mg, 54%).

Workup

  1. customat 80° C.
  2. customfor 3 hrs

Sources & evidence

ORD record
ord-b238a72f5a22442596d91d3a15eee2ff
Source dataset
uspto-grants-2016_04
Patent number
US09321776B2

Reaction notes

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