Dimethyl Sulfate → HCID 57600245, compound

HRID 1664504Notes

Reaction equation

HRID 1664504 reaction equation
[CH2:1]([N:6]1[C:14]2[N:13]=[C:12]([C:15]([F:18])([F:17])[F:16])[NH:11][C:10]=2[C:9](=[O:19])[NH:8][C:7]1=[S:20])[CH2:2][CH2:3][CH2:4][CH3:5].[OH-].[Na+].S(OC)(O[CH3:27])(=O)=O>O>[CH3:27][S:20][C:7]1[N:6]([CH2:1][CH2:2][CH2:3][CH2:4][CH3:5])[C:14]2[N:13]=[C:12]([C:15]([F:18])([F:16])[F:17])[NH:11][C:10]=2[C:9](=[O:19])[N:8]=1

Participants

5

Reactant 3

HCID 6497Dimethyl SulfateHCID 14798Sodium HydroxideHCID 57600153HCID 57600153, compound

Product 1

HCID 57600245HCID 57600245, compoundYield 95.6%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To the solution of 3-pentyl-2-thioxo-8-(trifluoromethyl)-1,2,3,7-tetrahydro-6H-purin-6-one (600 mg, 2 mmol) in a 2 M solution of sodium hydroxide in water (12.0 mL) was added dimethyl sulfate (0.30 mL, 3.2 mmol). The reaction mixture was stirred at room temperature for 1.5 h and quenched with acetic acid. The resulting solution was extracted with methylene chloride three times. The combined organic layer was dried, filtered and concentrated to give the desired product (0.60 g, 95.6%). LCMS calculated for C12H16F3N4OS: (M+H) 321.1. found 321.1.

Workup

  1. customquenched with acetic acid
  2. extractionThe resulting solution was extracted with methylene chloride three times
  3. customThe combined organic layer was dried
  4. filtrationfiltered
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-9a1bc62a4a5e47aaabec97f7c3f19a12
Source dataset
uspto-grants-2011_10
Patent number
US08039478B2

Reaction notes

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