Acetic Acid → 2-(methylthio)-3-pentyl-3,7-dihydro-6H-purin-6-one

HRID 1664573Notes

Reaction equation

HRID 1664573 reaction equation
[CH2:1]([N:6]1[C:14]2[N:13]=[CH:12][NH:11][C:10]=2[C:9](=[O:15])[NH:8][C:7]1=[S:16])[CH2:2][CH2:3][CH2:4][CH3:5].S(OC)(O[CH3:21])(=O)=O.C(O)(=O)C>[OH-].[Na+].O>[CH3:21][S:16][C:7]1[N:6]([CH2:1][CH2:2][CH2:3][CH2:4][CH3:5])[C:14]2[N:13]=[CH:12][NH:11][C:10]=2[C:9](=[O:15])[N:8]=1

Participants

6

Reactant 3

HCID 176Acetic AcidHCID 6497Dimethyl SulfateHCID 576002363-Pentyl-2-thioxo-1,2,3,7-tetrahydro-6H-purin-6-one

Product 1

HCID 576002282-(methylthio)-3-pentyl-3,7-dihydro-6H-purin-6-oneYield 40%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 14798Sodium HydroxideSolvent

Procedure

To a solution of 3-pentyl-2-thioxo-1,2,3,7-tetrahydro-6H-purin-6-one (13.0 g, 54.6 mmol) in 2 M of sodium hydroxide in water (250 mL) was added dimethyl sulfate (6.2 mL, 66 mmol), and the reaction mixture was stirred at room temperature for 1 hour, then neutralized with acetic acid. The precipitate was collected by filtration and recrystallized from ethyl acetate-MeOH (1:1) to give the desired product (5.50 g, 40%). LCMS calculated for C11H17N4OS (M+H): 253.1. found: 253.1.

Workup

  1. filtrationThe precipitate was collected by filtration
  2. customrecrystallized from ethyl acetate-MeOH (1:1)

Sources & evidence

ORD record
ord-9c89164bd9744ea9ab08106c28a8f1e8
Source dataset
uspto-grants-2011_10
Patent number
US08039478B2

Reaction notes

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