Potassium Carbonate → N2-Butyl-9-(4-chlorobutyl)-8-(methyloxy)-9H-purine-2,6-diamine

HRID 590429Notes

Reaction equation

HRID 590429 reaction equation
FC(F)(F)C(O)=O.[CH2:8]([NH: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][CH2:33][CH2:34][CH2:35][Cl:36]>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][CH2:35][Cl:36])=[C:15]([NH2:24])[N:14]=1)[CH2:9][CH2:10][CH3:11]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 813641-Bromo-4-chlorobutaneHCID 178448879HCID 178448879, compound

Product 1

HCID 59252596N2-Butyl-9-(4-chlorobutyl)-8-(methyloxy)-9H-purine-2,6-diamineYield 109.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
50 °C

Procedure

N2-Butyl-8-(methyloxy)-9H-purine-2,6-diamine trifluoroacetate (5 g, 14.27 mmol) and potassium carbonate (4.93 g, 35.7 mmol) were suspended in DMF (40 ml) and heated to 50° C. under nitrogen for 30 mins. The mixture was cooled to room temperature, 1-bromo-4-chlorobutane (1.645 ml, 14.27 mmol) was added and stirring was continued at room temperature for 20 hours. The solvent was concentrated under vacuum and the residue was partitioned between DCM (100 ml) and water (100 ml). The layers were separated using a hydrophobic frit and the aqueous phase was re-extracted with DCM (100 ml). The combined organics extracts were concentrated in vacuo and the residue purified by chromatography using a FlashMaster apparatus (100 g silica cartridge) and using a DCM:methanol 0-25% gradient over 40 mins. The desired fractions were combined and concentrated under vacuum to give the impure title compound as a yellow oil (5.1 g).

Workup

  1. temperatureThe mixture was cooled to room temperature
  2. concentrationThe solvent was concentrated under vacuum
  3. customthe residue was partitioned between DCM (100 ml) and water (100 ml)
  4. customThe layers were separated
  5. extractionthe aqueous phase was re-extracted with DCM (100 ml)
  6. concentrationThe combined organics extracts were concentrated in vacuo
  7. customthe residue purified by chromatography
  8. waitmethanol 0-25% gradient over 40 mins
  9. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-02f9f37d7b9b48a590c70d6cf5e384cd
Source dataset
uspto-grants-2016_01
Patent number
US09233962B2

Reaction notes

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