Potassium Carbonate → N2-Butyl-8-(methoxy)-9-(tetrahydro-3-furanylmethyl)-9H-Purine-2,6-diamine

HRID 1011060Notes

Reaction equation

HRID 1011060 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][CH:33]1[CH2:37][CH2:36][O:35][CH2:34]1>CN(C=O)C.O.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][CH:33]2[CH2:37][CH2:36][O:35][CH2:34]2)=[C:15]([NH2:24])[N:14]=1)[CH2:9][CH2:10][CH3:11]

Participants

7

Reactant 3

HCID 11430Potassium CarbonateHCID 141734223-(Bromomethyl)oxolaneHCID 178448877HCID 178448877, compound

Product 1

HCID 57699650N2-Butyl-8-(methoxy)-9-(tetrahydro-3-furanylmethyl)-9H-Purine-2,6-diamineYield 45.6%

Reagents, catalysts & solvents 3

HCID 702EthanolSolventHCID 962WaterSolvent2×HCID 6228DimethylformamideSolvent

Procedure

N2-Butyl-8-(methoxy)-3H-purine-2,6-diamine trifluoroacetic acid salt (0.25 g) and anhydrous potassium carbonate (0.395 g) in anhydrous DMF (3 mL) was heated for 1 hour at 60° C. (external) under nitrogen, before being allowed to cool to room temperature. To the reaction mixture was then added 3-(bromomethyl) tetrahydrofuran (0.236 g) and the reaction mixture heated under nitrogen to 50° C. (external) for 18.5 hours. The reaction mixture was then diluted with water (15 mL) and extracted with diethyl ether (15 mL, 3 times). The organic layers were combined and dried over anhydrous sodium sulphate. The sodium sulphate was filtered off and the filtrate evaporated under reduced pressure to give an oil. This oil was triturated with cyclohexane and a little diethyl ether to give a solid. The cyclohexane and diethyl ether was evaporated under reduced pressure to give a white solid. The solid (0.2606 g) was dissolved in hot ethanol (2 mL). To this solution was then added water (8 mL) and the resultant suspension was heated to reflux (93° C., external) giving a solution. The solution was then allowed to cool slowly (by not removing the flask from the reaction block and turning the power off to the heating block). This gave a solid gum on cooling which when sonicated gave a white solid. This solid was isolated by filtration under suction and then dried under vacuo at 50° C., overnight. This gave the title compound (0.1043 g) as a white solid.

Workup

  1. extractionextracted with diethyl ether (15 mL, 3 times)
  2. dry with materialdried over anhydrous sodium sulphate
  3. filtrationThe sodium sulphate was filtered off
  4. customthe filtrate evaporated under reduced pressure
  5. customto give an oil
  6. customThis oil was triturated with cyclohexane
  7. customa little diethyl ether to give a solid
  8. customThe cyclohexane and diethyl ether was evaporated under reduced pressure
  9. customto give a white solid
  10. temperatureto reflux (93° C., external)
  11. customgiving a solution
  12. temperatureto cool slowly (by not
  13. customremoving the flask from the reaction block
  14. customThis gave a solid gum
  15. temperatureon cooling which when
  16. customsonicated
  17. customgave a white solid
  18. customThis solid was isolated by filtration under suction
  19. customdried under vacuo at 50° C., overnight

Sources & evidence

ORD record
ord-60cae1d124d1447298c5329412e03934
Source dataset
uspto-grants-2011_07
Patent number
US07977344B2

Reaction notes

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