Potassium Carbonate → HCID 57699826, compound

HRID 1011039Notes

Reaction equation

HRID 1011039 reaction equation
FC(F)(F)C(O)=O.[CH3:8][CH:9]([O:11][CH2:12][CH2:13][O:14][C:15]1[N:23]=[C:22]2[C:18]([N:19]=[C:20]([O:24][CH3:25])[NH:21]2)=[C:17]([NH2:26])[N:16]=1)[CH3:10].C(=O)([O-])[O-].[K+].[K+].CS(O[CH2:38][CH:39]1[CH2:44][CH2:43][O:42][CH2:41][CH2:40]1)(=O)=O>CN(C)C=O.C(OCC)(=O)C>[CH3:10][CH:9]([O:11][CH2:12][CH2:13][O:14][C:15]1[N:23]=[C:22]2[C:18]([N:19]=[C:20]([O:24][CH3:25])[N:21]2[CH2:38][CH:39]2[CH2:44][CH2:43][O:42][CH2:41][CH2:40]2)=[C:17]([NH2:26])[N:16]=1)[CH3:8]

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 15166436Oxan-4-ylmethyl methanesulfonateHCID 178493998HCID 178493998, compound

Product 1

HCID 57699826HCID 57699826, compoundYield 112.7%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
60 °C

Procedure

To a solution of 2-({2-[(1-methylethyl)oxy]ethyl}oxy)-8-(methoxy)-9H-purin-6-amine trifluoroacetate salt (400 mg) in dry N,N-dimethylformamide (6.4 ml) was added potassium carbonate (579 mg). The reaction was stirred at 60° C. for 1.5 hours. The reaction was cooled and tetrahydro-2H-pyran-4-ylmethyl methanesulfonate (224 mg) was added. The reaction was stirred at 90° C. for 4 hours. The reaction was cooled and taken up in ethyl acetate and washed twice with water. The organic layer was separated, dried over magnesium sulphate, filtered and concentrated in vacuo to yield a yellow oil (432 mg). The product was purified by C18 reverse phase chromatography using water (containing 0.1% formic acid)-acetonitrile (containing 0.05% formic acid) as eluant (20-50%) to afford the title compound as a clear viscous oil (166 mg).

Workup

  1. temperatureThe reaction was cooled
  2. stirringThe reaction was stirred at 90° C. for 4 hours
  3. temperatureThe reaction was cooled
  4. washwashed twice with water
  5. customThe organic layer was separated
  6. dry with materialdried over magnesium sulphate
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-f36145ade31a4edea4995b80fa408bfc
Source dataset
uspto-grants-2011_07
Patent number
US07977344B2

Reaction notes

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