Potassium Carbonate → HCID 178519204, compound

HRID 634439Notes

Reaction equation

HRID 634439 reaction equation
Br[CH2:2][C:3]1[O:4][C:5](=[O:19])[C:6]2[C:11]([C:12]=1[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)=[CH:10][CH:9]=[CH:8][CH:7]=2.O.[N:21]1[C:29]([SH:30])=[C:28]2[C:24]([NH:25][CH:26]=[N:27]2)=[N:23][CH:22]=1.C([O-])([O-])=O.[K+].[K+]>CN(C=O)C.O>[N:21]1[C:29]([S:30][CH2:2][C:3]2[O:4][C:5](=[O:19])[C:6]3[C:11]([C:12]=2[C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)=[CH:10][CH:9]=[CH:8][CH:7]=3)=[C:28]2[C:24]([NH:25][CH:26]=[N:27]2)=[N:23][CH:22]=1

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 1181311893-(Bromomethyl)-4-phenyl-1H-isochromen-1-one2×HCID 178527205HCID 178527205, compound

Product 1

HCID 178519204HCID 178519204, compoundYield 56%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

3-(Bromomethyl)-4-phenyl-1H-isochromen-1-one (Intermediate C1, 35 mg, 0.111 mmol), 9H-purine-6-thiol hydrate (18.9 mg, 0.111 mmol) and K2CO3 (15.35 mg, 0.111 mmol) were dissolved in DMF (1 ml) and stirred at RT for 1 hrs 30 min. The reaction mixture was then diluted with water (10 ml) and 0.1 N HClaqueous (1 ml). The mixture was extracted with EtOAc and the collected organic phases were dried over Na2SO4, filtered and concentrated under reduced pressure. The crude was purified by Preparative HPLC (method 2) to give the title compound (24 mg, 56%).

Workup

  1. extractionThe mixture was extracted with EtOAc
  2. dry with materialthe collected organic phases were dried over Na2SO4
  3. filtrationfiltered
  4. concentrationconcentrated under reduced pressure
  5. customThe crude was purified by Preparative HPLC (method 2)

Sources & evidence

ORD record
ord-2e2693ba0a4246478fd06df5a5826971
Source dataset
uspto-grants-2016_04
Patent number
US09321776B2

Reaction notes

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