Potassium Carbonate → HCID 57699757, compound

HRID 1010955Notes

Reaction equation

HRID 1010955 reaction equation
FC(F)(F)C(O)=O.[CH3:8][O:9][C:10]1[NH:11][C:12]2[C:17]([N:18]=1)=[C:16]([NH2:19])[N:15]=[C:14]([NH:20][CH2:21][CH2:22][CH2:23][CH2:24][CH3:25])[N:13]=2.C(=O)([O-])[O-].[K+].[K+].Br[CH2:33][CH:34]1[CH2:39][CH2:38][O:37][CH2:36][CH2:35]1>CN(C=O)C.CCOC(C)=O>[CH3:8][O:9][C:10]1[N:11]([CH2:33][CH:34]2[CH2:39][CH2:38][O:37][CH2:36][CH2:35]2)[C:12]2[C:17]([N:18]=1)=[C:16]([NH2:19])[N:15]=[C:14]([NH:20][CH2:21][CH2:22][CH2:23][CH2:24][CH3:25])[N:13]=2

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 27732864-(Bromomethyl)oxaneHCID 178446274HCID 178446274, compound

Product 1

HCID 57699757HCID 57699757, compoundYield 65.6%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 8-methoxy-N2-pentyl-9H-purine-2,6-diamine trifluoroacetic acid salt (223 mg) in dry DMF (3.85 mL) was added potassium carbonate (339 mg) at 60° C. and the mixture was stirred for 90 mins. The mixture was cooled to room temperature and 4-(bromomethyl)tetrahydro-2H-pyran (121 mg) was added in one portion. The reaction was stirred at 50° C. overnight and was then cooled and taken up in EtOAc (20 mL). The organics were washed with water (2×10 mL), separated, dried over MgSO4, filtered and concentrated in vacuo to give an off-white solid. The crude material was purified by C18 reverse phase chromatography (ISCO) using water (0.1% formic acid)-acetonitrile (0.05% formic acid) as eluent (20-60%) to afford the title compound as an off-white solid (140 mg).

Workup

  1. stirringThe reaction was stirred at 50° C. overnight
  2. temperaturewas then cooled
  3. washThe organics were washed with water (2×10 mL)
  4. customseparated
  5. dry with materialdried over MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. customto give an off-white solid
  9. customThe crude material was purified by C18 reverse phase chromatography (ISCO)

Sources & evidence

ORD record
ord-2a023d030b4a4ae19a7bd53ee80d94c2
Source dataset
uspto-grants-2011_07
Patent number
US07977344B2

Reaction notes

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