Dimethylformamide → N2-Butyl-8-(methyloxy)-9-[4-(tetrahydro-2-furanyl)butyl]-9H-purine-2,6-diamine

HRID 1011077Notes

Reaction equation

HRID 1011077 reaction equation
F[C:2](F)(F)[C:3](O)=O.C(O[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)CCC.[C:25](=O)([O-])[O-].[K+].[K+].Br[CH2:32][CH2:33][CH2:34][CH2:35][CH:36]1[CH2:40][CH2:39][CH2:38][O:37]1.C[N:42]([CH:44]=O)C>>[CH2:44]([NH:42][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][CH:36]2[CH2:40][CH2:39][CH2:38][O:37]2)=[C:15]([NH2:24])[N:14]=1)[CH2:25][CH2:2][CH3:3]

Participants

5

Reactant 4

HCID 6228DimethylformamideHCID 11430Potassium CarbonateHCID 130669422-(4-Bromobutyl)oxolaneHCID 178450357HCID 178450357, compound

Product 1

HCID 57699577N2-Butyl-8-(methyloxy)-9-[4-(tetrahydro-2-furanyl)butyl]-9H-purine-2,6-diamine

Procedure

2-(Butyloxy)-8-(methyloxy)-1H-purin-6-amine trifluoroacetate (120 mg, 0.342 mmol) was heated with potassium carbonate (189 mg, 1.366 mmol) in dry DMF (5 ml) at 60° C. for 1 hour and then cooled to room temperature. 2-(4-Bromobutyl)tetrahydrofuran (82 mg, 0.394 mmol) was added and the reaction mixture heated at 50° C. under nitrogen for 16 hours and then partitioned between water (2 ml) and DCM (5 ml). The aqueous layer was further extracted with DCM (2×5 ml) and the combined organic layers were dried by passage through a hydrophobic frit and evaporated to dryness using a nitrogen blowdown unit. The residue was dissolved in methanol (0.6 ml) and purified by mass directed autopreparation. Product containing fractions were combined and evaporated to dryness in a nitrogen blowdown apparatus to give the title compound (76 mg).

Workup

  1. temperaturethe reaction mixture heated at 50° C. under nitrogen for 16 hours
  2. custompartitioned between water (2 ml) and DCM (5 ml)
  3. extractionThe aqueous layer was further extracted with DCM (2×5 ml)
  4. customthe combined organic layers were dried by passage through a hydrophobic frit
  5. customevaporated to dryness
  6. dissolutionThe residue was dissolved in methanol (0.6 ml)
  7. custompurified by mass
  8. additionProduct containing fractions
  9. customevaporated to dryness in a nitrogen blowdown apparatus

Sources & evidence

ORD record
ord-4917ff296f944edcaacfa7aec8c148b1
Source dataset
uspto-grants-2011_07
Patent number
US07977344B2

Reaction notes

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