Hydrochloric Acid → 6-Amino-2-[(tetrahydro-2-furanylmethyl)oxy]-9-(tetrahydro-2H-pyran-4-ylmethyl)-7,9-dihydro-8H-Purin-8-one

HRID 1011190Notes

Reaction equation

HRID 1011190 reaction equation
C[O:2][C:3]1[N:4]([CH2:20][CH:21]2[CH2:26][CH2:25][O:24][CH2:23][CH2:22]2)[C:5]2[C:10]([N:11]=1)=[C:9]([NH2:12])[N:8]=[C:7]([O:13][CH2:14][CH:15]1[CH2:19][CH2:18][CH2:17][O:16]1)[N:6]=2.Cl.[OH-].[Na+]>CO.O1CCOCC1>[NH2:12][C:9]1[N:8]=[C:7]([O:13][CH2:14][CH:15]2[CH2:19][CH2:18][CH2:17][O:16]2)[N:6]=[C:5]2[C:10]=1[NH:11][C:3](=[O:2])[N:4]2[CH2:20][CH:21]1[CH2:26][CH2:25][O:24][CH2:23][CH2:22]1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 576996338-(Methoxy)-2-[(tetrahydro-2-furanylmethyl)oxy]-9-(tetrahydro-2H-Pyran-4-ylmethyl)-9H-purin-6-amine

Product 1

HCID 576997746-Amino-2-[(tetrahydro-2-furanylmethyl)oxy]-9-(tetrahydro-2H-pyran-4-ylmethyl)-7,9-dihydro-8H-Purin-8-oneYield 78.4%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 312751,4-DioxaneSolvent

Procedure

8-(Methoxy)-2-[(tetrahydro-2-furanyl methyl)oxy]-9-(tetrahydro-2H-pyran-4-ylmethyl)-9H-purin-6-amine (0.1500 g) was dissolved in methanol (10 mL). To this solution was added 4N hydrogen chloride in 1,4-dioxane (2 mL). The reaction mixture was stirred for 5 hours at room temperature. The reaction mixture was evaporated under reduced pressure and then water (3 mL) and methanol (3 mL) was added to the residue to give a finely divided suspension. This was neutralised (to pH 7) by the addition of 2N sodium hydroxide and then evaporated under reduced pressure to dryness. Water (3 mL) was then added to the residue and the resultant white suspension of solid was isolated by filtration under suction. The solid was washed with methanol (1 mL) and then air-dried under suction. The solid was then dried further to constant weight under vacuo at 50° C. (˜1 hour). This gave the title compound as a white solid (0.1130 g)

Workup

  1. customThe reaction mixture was evaporated under reduced pressure
  2. additionwater (3 mL) and methanol (3 mL) was added to the residue
  3. customto give a finely divided suspension
  4. customevaporated under reduced pressure to dryness
  5. additionWater (3 mL) was then added to the residue
  6. additionthe resultant white suspension of solid
  7. customwas isolated by filtration under suction
  8. washThe solid was washed with methanol (1 mL)
  9. customair-dried under suction
  10. customThe solid was then dried further to constant weight under vacuo at 50° C. (˜1 hour)

Sources & evidence

ORD record
ord-b9f300880d38435798995279a2b01dfa
Source dataset
uspto-grants-2011_07
Patent number
US07977344B2

Reaction notes

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