Hydrochloric Acid → 6-Amino-2-butoxy-9-[2-(tetrahydro-2H-pyran-3-yl)ethyl]-7,9-dihydro-8H-Purin-8-one

HRID 1011160Notes

Reaction equation

HRID 1011160 reaction equation
[CH2:1]([O:5][C:6]1[N:14]=[C:13]2[C:9]([N:10]=[C:11]([O:23]C)[N:12]2[CH2:15][CH2:16][CH:17]2[CH2:22][CH2:21][CH2:20][O:19][CH2:18]2)=[C:8]([NH2:25])[N:7]=1)[CH2:2][CH2:3][CH3:4].Cl>CO.O1CCOCC1>[NH2:25][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:23])[N:12]2[CH2:15][CH2:16][CH:17]1[CH2:22][CH2:21][CH2:20][O:19][CH2:18]1

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 576997412-Butoxy-8-methoxy-9-[2-(tetrahydro-2H-pyran-3-yl)ethyl]-9H-purin-6-amine

Product 1

HCID 250253626-Amino-2-butoxy-9-[2-(tetrahydro-2H-pyran-3-yl)ethyl]-7,9-dihydro-8H-Purin-8-oneYield 63.7%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 312751,4-DioxaneSolvent

Procedure

2-Butoxy-8-methoxy-9-[2-(tetrahydro-2H-pyran-3-yl)ethyl]-9H-purin-6-amine (108 mg) was dissolved in methanol (2 ml) and 4N hydrogen chloride in dioxan (1 ml) added. After 16 h the reaction mixture was stripped, quenched with water then saturated sodium hydrogen carbonate added, when a solid precipitated. This was filtered, washed with water and dried. The solid was treated with hot methanol and was filtered after allowing to cool to yield 66 mg of the title compound.

Workup

  1. customquenched with water
  2. additionsaturated sodium hydrogen carbonate added
  3. customwhen a solid precipitated
  4. filtrationThis was filtered
  5. washwashed with water
  6. customdried
  7. additionThe solid was treated with hot methanol
  8. filtrationwas filtered
  9. temperatureto cool

Sources & evidence

ORD record
ord-84beb7b2fea54b2d8a7948b9c0f0fd70
Source dataset
uspto-grants-2011_07
Patent number
US07977344B2

Reaction notes

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