Potassium Carbonate → N2-Butyl-8-(methyloxy)-9-[3-(tetrahydro-2H-pyran-4-yl)propyl]-9H-purine-2,6-diamine

HRID 1011084Notes

Reaction equation

HRID 1011084 reaction equation
[CH2:1]([NH:5][C:6]1[NH:14][C:13]2[C:9]([N:10]=[C:11]([O:15][CH3:16])[N:12]=2)=[C:8]([NH2:17])[N:7]=1)[CH2:2][CH2:3][CH3:4].C(=O)([O-])[O-].[K+].[K+].Br[CH2:25][CH2:26][CH2:27][CH:28]1[CH2:33][CH2:32][O:31][CH2:30][CH2:29]1>CN(C=O)C>[CH2:1]([NH:5][C:6]1[N:14]=[C:13]2[C:9]([N:10]=[C:11]([O:15][CH3:16])[N:12]2[CH2:25][CH2:26][CH2:27][CH:28]2[CH2:33][CH2:32][O:31][CH2:30][CH2:29]2)=[C:8]([NH2:17])[N:7]=1)[CH2:2][CH2:3][CH3:4]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 576997044-(3-Bromopropyl)oxaneHCID 178448876HCID 178448876, compound

Product 1

HCID 57699840N2-Butyl-8-(methyloxy)-9-[3-(tetrahydro-2H-pyran-4-yl)propyl]-9H-purine-2,6-diamineYield 59.9%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
60 °C

Procedure

A mixture of N2-butyl-8-(methyloxy)-3H-purine-2,6-diamine (150 mg, 0.429 mmol) and potassium carbonate (237 mg, 1.718 mmol) in dry DMF (5 ml) was stirred at 60° C. for 1 hour under an atmosphere of nitrogen and then cooled to room temperature. 4-(3-Bromopropyl)tetrahydro-2H-pyran (0.087 ml, 0.515 mmol) was added and the mixture stirred at 50° C. overnight. The mixture was cooled and partitioned between 1:1 ethyl acetate:DCM (10 ml) and water (10 ml). The organic phase was separated using a hydrophobic frit and evaporated under a stream of nitrogen using a blowdown apparatus. The residue was dissolved in 1:1 methanol:DCM (2.8 ml) and purified by mass directed autopreparation. Product containing fractions were evaporated under a stream of nitrogen to give the title compound as a white solid (93.13 mg).

Workup

  1. temperaturecooled to room temperature
  2. stirringthe mixture stirred at 50° C. overnight
  3. temperatureThe mixture was cooled
  4. custompartitioned between 1:1 ethyl acetate
  5. customThe organic phase was separated
  6. customevaporated under a stream of nitrogen using a blowdown apparatus
  7. dissolutionThe residue was dissolved in 1:1 methanol
  8. customDCM (2.8 ml) and purified by mass
  9. additionProduct containing fractions
  10. customwere evaporated under a stream of nitrogen

Sources & evidence

ORD record
ord-67ff11036e154a6c9c8e381ebf3fbf7c
Source dataset
uspto-grants-2011_07
Patent number
US07977344B2

Reaction notes

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