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Potassium Carbonate → 2-Butyloxy-8-methoxy-9-[2-(tetrahydro-2H-pyran-2-yl)ethyl]-9H-Purin-6-amine

HRID 1010984
Notes
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Reaction equation

HRID 1010984 reaction equation
FC(F)(F)C(O)=O.[CH2:8]([O: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][CH:38]1[CH2:43][CH2:42][CH2:41][CH2:40][O:39]1)(=O)=O>CN(C=O)C>[CH2:8]([O: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][CH:38]2[CH2:43][CH2:42][CH2:41][CH2:40][O:39]2)=[C:15]([NH2:24])[N:14]=1)[CH2:9][CH2:10][CH3:11]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 576998282-(Oxan-2-yl)ethyl methanesulfonateHCID 178450370HCID 178450370, compound

Product 1

HCID 576998182-Butyloxy-8-methoxy-9-[2-(tetrahydro-2H-pyran-2-yl)ethyl]-9H-Purin-6-amineYield 44.2%

Reagents, catalysts & solvents 1

HCID 6228Dimethylformamide
Solvent

Conditions

Temperature
60 °C

Procedure

A mixture of 2-butoxy-8-methoxy-9H-purin-6-amine trifluoroacetate salt (200 mg) and potassium carbonate (236 mg) in dry DMF (2 mL) were heated at 60° C. with stirring for 1 h. 2-(Tetrahydro-2H-pyran-2-yl)ethyl methanesulfonate (142 mg) was added and the reaction was continued for 16 h at 60° C. The mixture was quenched with water and extracted with EtOAc (×3). The combined organics were washed with water and brine, dried using a hydrophobic frit and evaporated to give crude material (540 mg). The material was purified by normal phase chromatography (ISCO) using 0-20% methanol/EtOAc as eluent to give the title compound as a white solid (88 mg).

Workup

  1. waitthe reaction was continued for 16 h at 60° C
  2. customThe mixture was quenched with water
  3. extractionextracted with EtOAc (×3)
  4. washThe combined organics were washed with water and brine
  5. customdried
  6. customevaporated
  7. customto give crude material (540 mg)
  8. customThe material was purified by normal phase chromatography (ISCO)

Sources & evidence

ORD record
ord-fd93985a397b4e18bcdcf7f23cd3d698
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