1,3-Dibromopropane → 2-(Butyloxy)-8-(methyloxy)-9-{3-[(tetrahydro-2-furanylmethyl)amino]propyl}-9H-purin-6-amine

HRID 2036343Notes

Reaction equation

HRID 2036343 reaction equation
FC(F)(F)C(O)=O.[CH2:8]([O:12][C:13]1[NH:14][C:15]([NH2:24])=[C:16]2[C:20]([N:21]=1)=[N:19][C:18]([O:22][CH3:23])=[N:17]2)[CH2:9][CH2:10][CH3:11].C([O-])([O-])=O.[K+].[K+].Br[CH2:32][CH2:33][CH2:34]Br.[O:36]1[CH2:40][CH2:39][CH2:38][CH:37]1[CH2:41][NH2:42].C(N(CC)CC)C>CN(C=O)C.[Cl-].[Na+].O.O>[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][CH2:33][CH2:34][NH:42][CH2:41][CH:37]2[CH2:38][CH2:39][CH2:40][O:36]2)=[C:15]([NH2:24])[N:14]=1)[CH2:9][CH2:10][CH3:11]

Participants

9

Reactant 5

HCID 80011,3-DibromopropaneHCID 8471TriethylamineHCID 11430Potassium CarbonateHCID 253298TetrahydrofurfurylamineHCID 178450357HCID 178450357, compound

Product 1

HCID 672115702-(Butyloxy)-8-(methyloxy)-9-{3-[(tetrahydro-2-furanylmethyl)amino]propyl}-9H-purin-6-amineYield 26.4%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6228DimethylformamideSolvent2×HCID 57417360Sodium chloride; waterSolvent

Conditions

Temperature
20 °C

Procedure

2-(Butyloxy)-8-(methyloxy)-1H-purin-6-amine trifluoroacetate (70 mg, 0.2 mmol) and K2CO3 (68.8 mg, 0.050 mmol) was stirred in DMF (2 ml) at 50° C. for 1 hour. The reaction was cooled and 1,3-dibromopropane (0.020 ml, 0.2 mmol) was added. The mixture was stirred at 20° C. for 40 mins. (Tetrahydro-2-furanylmethyl)amine (0.41 ml, 0.2 mmol) and triethylamine (0.056 ml, 0.4 mmol) in DMF (1 ml) was added and the reaction mixture stirred at rt for 16 hours. Water (2 ml) and brine (2 ml) were added to the mixture. The product was extracted with DCM (2×5 ml) using a hydrophobic separation cartridge and the solvent removed on the N2 blowdown unit. The sample was dissolved in 1:1 MeOH:DMSO (1 ml) and purified by Mass Directed AutoPrep (Method A). The solvent was dried under a stream of nitrogen to give the title compound as a white solid (20 mg).

Workup

  1. temperatureThe reaction was cooled
  2. stirringthe reaction mixture stirred at rt for 16 hours
  3. extractionThe product was extracted with DCM (2×5 ml)
  4. customthe solvent removed on the N2 blowdown unit
  5. dissolutionThe sample was dissolved in 1:1 MeOH
  6. customDMSO (1 ml) and purified by Mass Directed AutoPrep (Method A)
  7. customThe solvent was dried under a stream of nitrogen

Sources & evidence

ORD record
ord-042c384d60fc427188fe0541dd8a47e5
Source dataset
uspto-grants-2013_11
Patent number
US08575181B2

Reaction notes

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