Hydrochloric Acid → 6-Amino-2-(butylamino)-9-(tetrahydro-3-furanylmethyl)-7,9-dihydro-8H-purin-8-one

HRID 1011153Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1011153
[CH2:1]([NH:5][C:6]1[N:14]=[C:13]2[C:9]([N:10]=[C:11]([O:21]C)[N:12]2[CH2:15][CH:16]2[CH2:20][CH2:19][O:18][CH2:17]2)=[C:8]([NH2:23])[N:7]=1)[CH2:2][CH2:3][CH3:4].Cl.O.[OH-].[Na+]>CO.O1CCOCC1.C(O)C>[NH2:23][C:8]1[N:7]=[C:6]([NH:5][CH2:1][CH2:2][CH2:3][CH3:4])[N:14]=[C:13]2[C:9]=1[NH:10][C:11](=[O:21])[N:12]2[CH2:15][CH:16]1[CH2:20][CH2:19][O:18][CH2:17]1

Komponenten

8

Edukt 4

HCID 313Hydrochloric AcidHCID 962Water4×HCID 14798Sodium HydroxideHCID 57699650N2-Butyl-8-(methoxy)-9-(tetrahydro-3-furanylmethyl)-9H-Purine-2,6-diamine

Produkt 1

HCID 250251656-Amino-2-(butylamino)-9-(tetrahydro-3-furanylmethyl)-7,9-dihydro-8H-purin-8-oneAusbeute 58,7 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 702EthanolLösungsmittelHCID 887MethanolLösungsmittel2×HCID 312751,4-DioxaneLösungsmittel

Versuchsvorschrift

N2-Butyl-8-(methoxy)-9-(tetrahydro-3-furanylmethyl)-9H-purine-2,6-diamine (98 mg) was dissolved in methanol (2 mL). To the resultant solution was added 4N hydrogen chloride in 1,4-dioxane (0.5 mL). The reaction mixture was then stirred at ambient temperature until completion (monitored by LCMS) over 2.5 hours. The reaction mixture was then evaporated under reduced pressure to give an oil. To this oil was added water (2 mL) and methanol (2 mL). The resultant solution was then neutralised using 2M sodium hydroxide solution. Further water (5 mL) was added when the product precipitated (pH 4-5). The white solid was isolated by filtration under suction and then washed with water (5 mL). The filter cake was then air-dried under suction to give (68 mg) that was dissolved in ethanol (2 mL). To this solution was added water (2 mL) to give a precipitate. The resultant suspension was heated (90° C., external) to reflux to give a solution. The resultant solution was refluxed for a few minutes before being allowed to cool to ambient room temperature to give a flocculent white solid. This solid was isolated by filtration under suction and the residues transferred using water (8 mL). The filter cake was air-dried under suction and was then dried under vacuo at 50° C. for 4 hours to give a white solid which was then transferred to a vial and dried further at 50° C. (16 hours) to give 55 mg of the title compound as a white solid.

Aufarbeitung

  1. customThe reaction mixture was then evaporated under reduced pressure
  2. customto give an oil
  3. customprecipitated (pH 4-5)
  4. customThe white solid was isolated by filtration under suction
  5. washwashed with water (5 mL)
  6. customThe filter cake was then air-dried under suction
  7. customto give (68 mg) that
  8. customto give a precipitate
  9. temperatureto reflux
  10. customto give a solution
  11. temperatureto cool to ambient room temperature
  12. customto give a flocculent white solid
  13. customThis solid was isolated by filtration under suction
  14. customThe filter cake was air-dried under suction
  15. customwas then dried under vacuo at 50° C. for 4 hours
  16. customto give a white solid which
  17. customdried further at 50° C. (16 hours)

Quellen und Nachweise

ORD-Eintrag
ord-022f6b52a8c0445d85b69a7e01861943
Quelldatensatz
uspto-grants-2011_07
Patentnummer
US07977344B2

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