Dimethyl Sulfate → HCID 57600245, compound

HRID 2368547Notes

Reaction equation

HRID 2368547 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-60592a8232dc4ef2a18bcfd730123ff4
Source dataset
uspto-grants-2014_04
Patent number
US08703783B2

Reaction notes

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