Dimethyl Sulfate → 7-Methyl-7,8-dihydroguanosine-5'-diphosphate

HRID 1799444Notes

Reaction equation

HRID 1799444 reaction equation
[P:1]([O:9][CH2:10][C@H:11]1[O:15][C@@H:14]([N:16]2[C:26]3[N:25]=[C:23]([NH2:24])[NH:22][C:20](=[O:21])[C:19]=3[N:18]=[CH:17]2)[C@H:13]([OH:27])[C@@H:12]1[OH:28])([O:4][P:5]([OH:8])([OH:7])=[O:6])(=[O:3])[OH:2].[Na].S(OC)(O[CH3:34])(=O)=O.[OH-].[Na+]>O.C(O)(=O)C>[P:1]([O:9][CH2:10][C@H:11]1[O:15][C@@H:14]([N:16]2[C:26]3[N:25]=[C:23]([NH2:24])[NH:22][C:20](=[O:21])[C:19]=3[N:18]([CH3:34])[CH2:17]2)[C@H:13]([OH:27])[C@@H:12]1[OH:28])([O:4][P:5]([OH:7])([OH:8])=[O:6])(=[O:2])[OH:3]

Participants

7

Reactant 4

HCID 6497Dimethyl SulfateHCID 14798Sodium HydroxideHCID 5360545SodiumHCID 135398619Guanosine Diphosphate

Product 1

HCID 1355091167-Methyl-7,8-dihydroguanosine-5'-diphosphate

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 962WaterSolvent

Procedure

In a clean, dry 2000 mL round bottom flask equipped with a stifling bar and under a stream of argon slowly dissolve dry and finely powdered guanosine 5′-diphosphate (1), (10.0 g, 20.5 mmol), either in free acid or sodium as a counter ion form, in 200 mL water, adjusting pH to 4.0 with glacial acetic acid. Dimethyl sulfate (20 mL, 119.04 mmol) was then added over a period of one hour with constant stirring at room temperature and the reaction continued for an additional hour during which time a decrease in pH was observed but pH was kept between pH 3.8 to 4.0 by drop-wise addition of 10 mM NaOH and methylation was monitored by analytical HPLC for progress. Methylation was determined to be 98% complete within 2 hr. After 2 hr, the reaction mixture was extracted with CHCl3 (3×200 mL) to remove unreacted excess dimethyl sulfate.

Workup

  1. customIn a clean, dry 2000 mL round bottom flask
  2. customequipped with a stifling bar and under a stream of argon
  3. dissolutionslowly dissolve
  4. customdry
  5. waitthe reaction continued for an additional hour during which time
  6. customcomplete within 2 hr
  7. extractionthe reaction mixture was extracted with CHCl3 (3×200 mL)
  8. customto remove unreacted excess dimethyl sulfate

Sources & evidence

ORD record
ord-8db4d0df7b3046e9a4eab12f00c6324d
Source dataset
uspto-grants-2013_01
Patent number
US08344118B2

Reaction notes

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