Potassium Carbonate → HCID 57699672, compound

HRID 1010927Notes

Reaction equation

HRID 1010927 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][CH2:35][O:34]1>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[CH2:32][CH:33]2[CH2:38][CH2:37][CH2:36][CH2:35][O:34]2)=[C:15]([NH2:24])[N:14]=1)[CH2:9][CH2:10][CH3:11]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 1419172-(Bromomethyl)tetrahydro-2H-pyranHCID 178450370HCID 178450370, compound

Product 1

HCID 57699672HCID 57699672, compoundYield 85%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

2-Butoxy-8-methoxy-9H-purin-6-amine trifluoroacetate salt (0.20 g) was heated with anhydrous potassium carbonate (0.315 g) in dry DMF (5 mL) at 60° C. for 1 hour and cooled to room temperature. 2-(Bromomethyl) tetrahydro-2H-pyran (73 uL) was added and the reaction mixture heated at 50° C., overnight. The reaction mixture was quenched into water (50 mL) and extracted into ethyl acetate (25 mL, 3 times). The combined organic layers were separated and passed through a hydrophobic frit to dry, then stripped to dryness and the pale yellow gum (145 mg), which turned to a white solid when triturated with methanol, was purified by MDAP to give the title compound (6 mg) (˜85% pure).

Workup

  1. temperaturethe reaction mixture heated at 50° C., overnight
  2. customThe reaction mixture was quenched into water (50 mL)
  3. extractionextracted into ethyl acetate (25 mL, 3 times)
  4. customThe combined organic layers were separated
  5. customto dry
  6. customtriturated with methanol
  7. customwas purified by MDAP

Sources & evidence

ORD record
ord-c099457dd756433f826a59dad3d84ff4
Source dataset
uspto-grants-2011_07
Patent number
US07977344B2

Reaction notes

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