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Potassium Carbonate → HCID 57699834, compound

HRID 1011038
Notes
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Reaction equation

HRID 1011038 reaction equation
FC(F)(F)C(O)=O.[CH2:8]([NH:12][C:13]1[N:21]=[C:20]2[C:16]([N:17]=[C:18]([O:22][CH3:23])[NH:19]2)=[C:15]([NH2:24])[N:14]=1)[CH2:9][CH2:10][CH3:11].C(=O)([O-])[O-].[K+].[K+].CS(O[CH2:36][CH2:37][CH2:38][CH:39]1[CH2:44][CH2:43][CH2:42][O:41][CH2:40]1)(=O)=O>CN(C)C=O.C(OCC)(=O)C>[CH2:8]([NH:12][C:13]1[N:21]=[C:20]2[C:16]([N:17]=[C:18]([O:22][CH3:23])[N:19]2[CH2:36][CH2:37][CH2:38][CH:39]2[CH2:44][CH2:43][CH2:42][O:41][CH2:40]2)=[C:15]([NH2:24])[N:14]=1)[CH2:9][CH2:10][CH3:11]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 57699683HCID 57699683, compoundHCID 178448879HCID 178448879, compound

Product 1

HCID 57699834HCID 57699834, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857
Ethyl Acetate
Solvent

Conditions

Temperature
60 °C

Procedure

To a solution of N2-butyl-8-methoxy-9H-purine-2,6-diamine trifluoroacetic acid salt (300 mg) in dry N,N-dimethylformamide (5.3 ml) was added potassium carbonate (474 mg). The reaction was stirred at 60° C. for ninety minutes. The reaction was cooled and 3-(tetrahydro-2H-pyran-3-yl)propyl methanesulfonate (209 mg) was added and the reaction heated at 90° C. for three hours. The reaction was cooled, diluted with ethyl acetate and washed with water (2×). The organic layer was separated, dried over magnesium sulphate, filtered and concentrated in vacuo. to afford a yellow oil. The product was purified by C18 reverse phase chromatography (43 g) (ISCO) using water (0.1% formic acid)-acetonitrile (0.05% formic acid) as eluant (30-80%) to afford the title compound as a yellow oily residue (198 mg).

Workup

  1. temperatureThe reaction was cooled
  2. temperaturethe reaction heated at 90° C. for three hours
  3. temperatureThe reaction was cooled
  4. washwashed with water (2×)
  5. customThe organic layer was separated
  6. dry with materialdried over magnesium sulphate
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo
  9. customto afford a yellow oil
  10. customThe product was purified by C18 reverse phase chromatography (43 g) (ISCO)

Sources & evidence

ORD record
ord-147c96f6182942f3a711d55339637081
Source dataset
uspto-grants-2011_07
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07977344B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes