Hydrochloric Acid → 6-Amino-2-butoxy-9-(tetrahydrofuran-3-ylmethyl)-7,9-dihydro-8H-purin-8-one

HRID 1011177Notes

Reaction equation

HRID 1011177 reaction equation
[CH2:1]([O: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>CO.O1CCOCC1>[NH2:23][C:8]1[N:7]=[C:6]([O: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

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 576996032-Butoxy-8-methoxy-9-(tetrahydrofuran-3-ylmethyl)-9H-purin-6-amine

Product 1

HCID 250251676-Amino-2-butoxy-9-(tetrahydrofuran-3-ylmethyl)-7,9-dihydro-8H-purin-8-oneYield 63.3%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 312751,4-DioxaneSolvent

Procedure

2-(Butyloxy)-8-(methoxy)-9-(tetrahydro-3-furanylmethyl)-9H-purin-6-amine (Isomer 1, 1.54 gm) was suspended in methanol (20 ml) and 4N HCl in dioxan (4 ml) added with stirring to give a clear solution. After 6.5 h, the solvents were evaporated to low volume and water added with stirring, followed by neutralisation with saturated sodium bicarbonate. The resulting off-white solid was filtered, washed with water and dried, yield 1.26 gm. This material was added portionwise to boiling methanol (130 ml), adding a further 20 ml of methanol. The suspension was filtered, and the solid treated with boiling methanol (20 ml) and added to the filtrate. This was reboiled, then allowed to cool with stirring when a white solid crystallised out. This was filtered, washed with methanol and dried, to give the title compound yield 932 mg.

Workup

  1. customto give a clear solution
  2. customthe solvents were evaporated to low volume and water
  3. additionadded
  4. stirringwith stirring
  5. filtrationThe resulting off-white solid was filtered
  6. washwashed with water
  7. customdried
  8. additionThis material was added portionwise
  9. additionadding a further 20 ml of methanol
  10. filtrationThe suspension was filtered
  11. additionthe solid treated with boiling methanol (20 ml)
  12. additionadded to the filtrate
  13. temperatureto cool
  14. stirringwith stirring when a white solid
  15. customcrystallised out
  16. filtrationThis was filtered
  17. washwashed with methanol
  18. customdried

Sources & evidence

ORD record
ord-34c52086a1064343b334edc762aff69b
Source dataset
uspto-grants-2011_07
Patent number
US07977344B2

Reaction notes

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