Potassium Carbonate → (4-(1H-indol-5-yloxy)pyrimidin-2-yl)methanol

HRID 450322Notes

Reaction equation

HRID 450322 reaction equation
C([O:4][CH2:5][C:6]1[N:11]=[C:10]([O:12][C:13]2[CH:14]=[C:15]3[C:19](=[CH:20][CH:21]=2)[NH:18][CH:17]=[CH:16]3)[CH:9]=[CH:8][N:7]=1)(=O)C.C([O-])([O-])=O.[K+].[K+]>CO.C(Cl)Cl.O>[NH:18]1[C:19]2[C:15](=[CH:14][C:13]([O:12][C:10]3[CH:9]=[CH:8][N:7]=[C:6]([CH2:5][OH:4])[N:11]=3)=[CH:21][CH:20]=2)[CH:16]=[CH:17]1

Participants

6

Reactant 2

HCID 11430Potassium CarbonateHCID 59394351(4-(1H-indol-5-yloxy)pyrimidin-2-yl)methyl acetate

Product 1

HCID 59394113(4-(1H-indol-5-yloxy)pyrimidin-2-yl)methanol

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 962WaterSolventHCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of (4-(1H-indol-5-yloxy)pyrimidin-2-yl)methyl acetate (0.51 g, 1.8 mmol) in MeOH (18 mL) at 0° C. is added solid K2CO3 (0.6 g, 4.5 mmol). The reaction is stirred for 30 minutes at 0° C. and then warmed to room temperature and stirred for an additional 30 minutes. The reaction mixture is then diluted with DCM and water and the layers are separated. The aqueous layer is extracted 2 additional times with DCM. The organic layers are combined dried over anhydrous Na2SO4, filtered, and concentrated to afford the title compound. MS (ESI) m/z 242.1 (M+1).

Workup

  1. temperaturewarmed to room temperature
  2. stirringstirred for an additional 30 minutes
  3. customthe layers are separated
  4. extractionThe aqueous layer is extracted 2 additional times with DCM
  5. dry with materialThe organic layers are combined dried over anhydrous Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-f41b93cdf5b24c23a7146ae562683797
Source dataset
uspto-grants-2013_07
Patent number
US08486954B2

Reaction notes

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