Potassium Carbonate → 2-Butoxy-8-methoxy-9-(tetrahydro-2H-pyran-3-ylmethyl)-9H-purin-6-amine

HRID 1010935Notes

Reaction equation

HRID 1010935 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+].Br[CH2:32][CH:33]1[CH2:38][CH2:37][CH2:36][O:35][CH2:34]1>CN(C)C=O>[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[CH2:32][CH:33]2[CH2:38][CH2:37][CH2:36][O:35][CH2:34]2)=[C:15]([NH2:24])[N:14]=1)[CH2:9][CH2:10][CH3:11]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 226172573-(Bromomethyl)oxaneHCID 178450370HCID 178450370, compound

Product 1

HCID 576996312-Butoxy-8-methoxy-9-(tetrahydro-2H-pyran-3-ylmethyl)-9H-purin-6-amineYield 55.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

2-Butoxy-8-methoxy-9H-purin-6-amine trifluoroacetate salt (0.2 g) in dry N,N-dimethylformamide (5 mL) was heated at 60° C. with anhydrous potassium carbonate (0.315 g) for 1 hour and allowed to cool to room temperature before adding 3-(bromomethyl)tetrahydro-2H-pyran (0.112 g). The reaction mixture was heated at 50° C., overnight. The reaction mixture was quenched with water (20 mL) and extracted into ethyl acetate (3 times, 75 mL combined volume). The organic phase was separated, combined and passed through a hydrophobic frit to dry. The organic phase was evaporated under reduced pressure to give a yellow oil which was purified by C18 reverse phase chromatography using water (containing 0.1% formic acid)-acetonitrile (containing 0.05% formic acid) as eluant (20-60%) to afford the title compound as a white solid (105.4 mg).

Workup

  1. temperatureThe reaction mixture was heated at 50° C., overnight
  2. customThe reaction mixture was quenched with water (20 mL)
  3. extractionextracted into ethyl acetate (3 times, 75 mL combined volume)
  4. customThe organic phase was separated
  5. customto dry
  6. customThe organic phase was evaporated under reduced pressure
  7. customto give a yellow oil which
  8. customwas purified by C18 reverse phase chromatography

Sources & evidence

ORD record
ord-49ec24286b7246e6a86a4a8f8685d499
Source dataset
uspto-grants-2011_07
Patent number
US07977344B2

Reaction notes

Loading…