Potassium Carbonate → N2-Butyl-8-(methyloxy)-9-[3-(tetrahydro-3-furanyl)propyl]-9H-purine-2,6-diamine

HRID 1011080Notes

Reaction equation

HRID 1011080 reaction equation
FC(F)(F)C(O)=O.[CH2:8]([NH:12][C:13]1[NH:21][C:20]2[C:16]([N:17]=[C:18]([O:22][CH3:23])[N:19]=2)=[C:15]([NH2:24])[N:14]=1)[CH2:9][CH2:10][CH3:11].C(=O)([O-])[O-].[K+].[K+].Br[CH2:32][CH2:33][CH2:34][CH:35]1[CH2:39][CH2:38][O:37][CH2:36]1>CN(C=O)C>[CH2:8]([NH:12][C:13]1[N:21]=[C:20]2[C:16]([N:17]=[C:18]([O:22][CH3:23])[N:19]2[CH2:32][CH2:33][CH2:34][CH:35]2[CH2:39][CH2:38][O:37][CH2:36]2)=[C:15]([NH2:24])[N:14]=1)[CH2:9][CH2:10][CH3:11]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 576997783-(3-Bromopropyl)oxolaneHCID 178448877HCID 178448877, compound

Product 1

HCID 57699816N2-Butyl-8-(methyloxy)-9-[3-(tetrahydro-3-furanyl)propyl]-9H-purine-2,6-diamineYield 56.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

N2-Butyl-8-(methyloxy)-3H-purine-2,6-diamine trifluoroacetate (150 mg, 0.428 mmol) was heated in dry DMF (2.5 ml) at 60° C. for 1 hour with potassium carbonate (237 mg, 1.713 mmol). The reaction mixture was cooled to room temperature and 3-(3-bromopropyl)tetrahydrofuran (99 mg, 0.514 mmol) was added. The mixture was then heated at 50° C. overnight. The reaction mixture was quenched with water (50 ml) and extracted with ethyl acetate (3×25 ml). The combined organic layers were separated and then dried by passage through a hydrophobic frit and evaporated to dryness. The residue was dissolved in 1:1 MeOH:DMSO (2.8 ml) and purified by mass directed autopreparation. Product containing fractions were evaporated under a stream of nitrogen in a blowdown apparatus to give the title compound as a clear gum (84 mg).

Workup

  1. temperatureThe mixture was then heated at 50° C. overnight
  2. customThe reaction mixture was quenched with water (50 ml)
  3. extractionextracted with ethyl acetate (3×25 ml)
  4. customThe combined organic layers were separated
  5. customdried by passage through a hydrophobic frit
  6. customevaporated to dryness
  7. dissolutionThe residue was dissolved in 1:1 MeOH
  8. customDMSO (2.8 ml) and purified by mass
  9. additionProduct containing fractions
  10. customwere evaporated under a stream of nitrogen in a blowdown apparatus

Sources & evidence

ORD record
ord-0da53e9b376a435f81e16c61d9a0e29e
Source dataset
uspto-grants-2011_07
Patent number
US07977344B2

Reaction notes

Loading…