Potassium Carbonate → 3-(1-(4-Amino-1H-pyrazolo[3,4-d]pyrimidin-1-yl)ethyl)-4-(6-methylpyridin-3-yl)-1H-isochromen-1-one

HRID 634444Notes

Reaction equation

HRID 634444 reaction equation
Br.Br[CH:3]([C:5]1[O:6][C:7](=[O:22])[C:8]2[C:13]([C:14]=1[C:15]1[CH:16]=[N:17][C:18]([CH3:21])=[CH:19][CH:20]=1)=[CH:12][CH:11]=[CH:10][CH:9]=2)[CH3:4].[NH:23]1[C:27]2=[N:28][CH:29]=[N:30][C:31]([NH2:32])=[C:26]2[CH:25]=[N:24]1.C([O-])([O-])=O.[K+].[K+]>CN(C=O)C>[NH2:32][C:31]1[N:30]=[CH:29][N:28]=[C:27]2[N:23]([CH:3]([C:5]3[O:6][C:7](=[O:22])[C:8]4[C:13]([C:14]=3[C:15]3[CH:16]=[N:17][C:18]([CH3:21])=[CH:19][CH:20]=3)=[CH:12][CH:11]=[CH:10][CH:9]=4)[CH3:4])[N:24]=[CH:25][C:26]=12

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 754201H-Pyrazolo[3,4-d]pyrimidin-4-amineHCID 1181314403-(1-Bromoethyl)-4-(6-methylpyridin-3-yl)-1H-isochromen-1-one hydrobromide

Product 1

HCID 1181312243-(1-(4-Amino-1H-pyrazolo[3,4-d]pyrimidin-1-yl)ethyl)-4-(6-methylpyridin-3-yl)-1H-isochromen-1-oneYield 15%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

3-(1-Bromoethyl)-4-(6-methylpyridin-3-yl)-1H-isochromen-1-one hydrobromide (intermediate C10, 120 mg, 0.282 mmol), 1H-pyrazolo[3,4-d]pyrimidin-4-amine (76 mg, 0.565 mmol), and K2CO3 (117 mg, 0.847 mmol) were stirred in DMF (1.5 ml) at 50° C. for 2.5 hrs. The reaction mixture was diluted with 1M HClaqueous (2 ml) and purified via reverse phase chromatography with a Biotage C18 SNAP column (Phase A, water 95%, ACN 5%, formic acid 0.1%); Phase B ACN 95%, water 5%, formic acid 0.1%) to give the title compound as colourless solid (16.7 mg, 15%).

Workup

  1. additionThe reaction mixture was diluted with 1M HClaqueous (2 ml)
  2. custompurified via reverse phase chromatography with a Biotage C18 SNAP column (Phase A, water 95%, ACN 5%, formic acid 0.1%)

Sources & evidence

ORD record
ord-15fd473e6c424213b0dfe3510adbc62e
Source dataset
uspto-grants-2016_04
Patent number
US09321776B2

Reaction notes

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