Dimethyl Sulfate → 7-Benzyl-6-(methylthio)-3-pentyl-3,7-dihydro-2H-purin-2-one

HRID 249764Notes

Reaction equation

HRID 249764 reaction equation
[CH2:1]([N:8]1[C:16]2[C:15](=[S:17])[NH:14][C:13](=[O:18])[N:12]([CH2:19][CH2:20][CH2:21][CH2:22][CH3:23])[C:11]=2[N:10]=[CH:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[OH-].[Na+].S(OC)(O[CH3:30])(=O)=O>O>[CH2:1]([N:8]1[C:16]2[C:15]([S:17][CH3:30])=[N:14][C:13](=[O:18])[N:12]([CH2:19][CH2:20][CH2:21][CH2:22][CH3:23])[C:11]=2[N:10]=[CH:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 6497Dimethyl SulfateHCID 14798Sodium HydroxideHCID 598538277-Benzyl-3-pentyl-6-thioxo-1,3,6,7-tetrahydro-2H-purin-2-one

Product 1

HCID 598538237-Benzyl-6-(methylthio)-3-pentyl-3,7-dihydro-2H-purin-2-oneYield 98%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
80 °C

Procedure

To a mixture of 7-benzyl-3-pentyl-6-thioxo-1,3,6,7-tetrahydro-2H-purin-2-one (5.3 g, 16 mmol) in a solution of sodium hydroxide in water (2 M, 50.0 mL) was added dimethyl sulfate (2.3 mL, 24 mmol). The reaction mixture was stirred at 80° C. overnight, quenched with acetic acid and extracted with dichloromethane (DCM). The organic layer was dried and concentrated to provide the desired product (5.2 g, 98% yield). LCMS calculated for C18H23N4OS (M+H): 343.2. found: 343.1.

Workup

  1. customquenched with acetic acid
  2. extractionextracted with dichloromethane (DCM)
  3. customThe organic layer was dried
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-62051289a0e540f29447078e9ab805e5
Source dataset
uspto-grants-2011_01
Patent number
US07863285B2

Reaction notes

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