Hydrochloric Acid → HCID 25025163, compound

HRID 1011152Notes

Reaction equation

HRID 1011152 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]C)[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][CH:33]1[CH2:37][CH2:36][CH2:35][O:34]1.Cl>CN(C)C=O.C(OCC)(=O)C.CO.O1CCOCC1>[NH2:24][C:15]1[N:14]=[C:13]([NH:12][CH2:8][CH2:9][CH2:10][CH3:11])[N:21]=[C:20]2[C:16]=1[NH:17][C:18](=[O:22])[N:19]2[CH2:32][CH:33]1[CH2:37][CH2:36][CH2:35][O:34]1

Participants

9

Reactant 4

HCID 313Hydrochloric AcidHCID 11430Potassium CarbonateHCID 14501Furan, 2-(bromomethyl)tetrahydro-HCID 178448879HCID 178448879, compound

Product 1

HCID 25025163HCID 25025163, compound

Reagents, catalysts & solvents 4

HCID 887MethanolSolventHCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolventHCID 312751,4-DioxaneSolvent

Conditions

Temperature
60 °C

Procedure

To a solution of N2-butyl-8-methoxy-9H-purine-2,6-diamine trifluoroacetic acid salt (400 mg) in dry N,N-dimethylformamide (6 ml) at room temperature and under nitrogen was added potassium carbonate (630 mg) in one go. The reaction was stirred at 60° C. for 1.5 hours and then cooled to 40° C. 2-(bromomethyl)tetrahydrofuran (156 μl) was added in one go and the reaction heated to 50° C. overnight and then at 90° C. for 2 hours. The reaction was diluted with ethyl acetate (20 ml) and washed with water (10 ml). The organic layer was separated and concentrated in vacuo. The product was semi-purified by MDAP to afford a mixture. To this mixture, in dry methanol (5 ml) at room temperature and under nitrogen was added 4.0M hydrogen chloride in 1,4-dioxane (1.5 ml) in one go. The reaction was left to stir at room temperature overnight. The reaction was concentrated in vacuo and the product purified by MDAP (slower-running isomer). This afforded the title compound as a white solid (15 mg).

Workup

  1. temperaturecooled to 40° C
  2. temperaturethe reaction heated to 50° C. overnight
  3. waitat 90° C. for 2 hours
  4. washwashed with water (10 ml)
  5. customThe organic layer was separated
  6. concentrationconcentrated in vacuo
  7. customto afford a mixture
  8. waitThe reaction was left
  9. stirringto stir at room temperature overnight
  10. concentrationThe reaction was concentrated in vacuo
  11. customthe product purified by MDAP (slower-running isomer)

Sources & evidence

ORD record
ord-9ca59579d49547ff944b9033faffb256
Source dataset
uspto-grants-2011_07
Patent number
US07977344B2

Reaction notes

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