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

HRID 45174Notes

Reaction equation

HRID 45174 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-815bbb2e92f84ec7ade7af15074b5b27
Source dataset
uspto-grants-2013_09
Patent number
US08541432B2

Reaction notes

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