Potassium Carbonate → HCID 57699705, compound

HRID 1011021Notes

Reaction equation

HRID 1011021 reaction equation
FC(F)(F)C(O)=O.[CH:8]1([CH2:14][O:15][C:16]2[N:24]=[C:23]3[C:19]([N:20]=[C:21]([O:25][CH3:26])[NH:22]3)=[C:18]([NH2:27])[N:17]=2)[CH2:13][CH2:12][CH2:11][CH2:10][CH2:9]1.C(=O)([O-])[O-].[K+].[K+].Br[CH2:35][CH:36]1[CH2:41][CH2:40][O:39][CH2:38][CH2:37]1>CN(C=O)C>[CH:8]1([CH2:14][O:15][C:16]2[N:24]=[C:23]3[C:19]([N:20]=[C:21]([O:25][CH3:26])[N:22]3[CH2:35][CH:36]3[CH2:41][CH2:40][O:39][CH2:38][CH2:37]3)=[C:18]([NH2:27])[N:17]=2)[CH2:9][CH2:10][CH2:11][CH2:12][CH2:13]1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 27732864-(Bromomethyl)oxaneHCID 178493990HCID 178493990, compound

Product 1

HCID 57699705HCID 57699705, compoundYield 62.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

2-[(Cyclohexylmethyl)oxy]-8-(methoxy)-9H-purin-6-amine trifluoroacetate salt (0.28 g) was heated with anhydrous potassium carbonate (0.3957 g) in anhydrous DMF (5 mL) under nitrogen for 1 hour at 60° C. (external). The reaction mixture was cooled to room temperature before adding 4-(bromomethyl) tetrahydro-2H-pyran (0.14 g) in anhydrous DMF (1 mL). The reaction mixture was heated to 50° C., overnight. The reaction mixture was quenched into water (20 mL) and extracted into ethyl acetate (20 mL, 3 times). The organic layers was separated, combined and then washed with brine (20 mL). The organic layer was separated and then dried by passing through a hydrophobic frit. Evaporation under reduced pressure gave pale yellow oil that solidified on standing. This was purified by C18 reverse phase chromatography using water (containing 0.1% formic acid)-acetonitrile (containing 0.05% formic acid) as eluent (30-80%) to give the title compound as a white solid (0.1677 g).

Workup

  1. temperatureThe reaction mixture was heated to 50° C., overnight
  2. customThe reaction mixture was quenched into water (20 mL)
  3. extractionextracted into ethyl acetate (20 mL, 3 times)
  4. customThe organic layers was separated
  5. washwashed with brine (20 mL)
  6. customThe organic layer was separated
  7. customdried
  8. customEvaporation under reduced pressure
  9. customgave pale yellow oil that solidified
  10. customThis was purified by C18 reverse phase chromatography

Sources & evidence

ORD record
ord-7c56632951114287bf4c97ed0aae732b
Source dataset
uspto-grants-2011_07
Patent number
US07977344B2

Reaction notes

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