Methanesulfonyl chloride → Methanesulfonic acid pyrimidin-5-ylmethyl ester

HRID 1865980Notes

Reaction equation

HRID 1865980 reaction equation
[N:1]1[CH:6]=[C:5]([CH2:7][OH:8])[CH:4]=[N:3][CH:2]=1.[CH3:9][S:10](Cl)(=[O:12])=[O:11]>CN(C1C=CN=CC=1)C.CCN(CC)CC>[N:1]1[CH:6]=[C:5]([CH2:7][O:8][S:10]([CH3:9])(=[O:12])=[O:11])[CH:4]=[N:3][CH:2]=1

Participants

5

Reactant 2

HCID 31297Methanesulfonyl chlorideHCID 15466386(Pyrimidin-5-yl)methanol

Product 1

HCID 86610239Methanesulfonic acid pyrimidin-5-ylmethyl esterYield 40%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 8471TriethylamineSolvent

Procedure

To a mixture of pyrimidin-5-yl-methanol, DMAP and NEt3 was slowly added MsCl at 0° C. and the reaction mixture was stirred at room temperature for 3 h. The reaction mixture was extracted with water and dichloromethane. The organic phase was dried on Na2SO4, filtered and the solvent was evaporated. Silica gel column chromatography (Ethyl acetate/hexane 1:1) gave the title compound in 40% yield.

Workup

  1. customat 0° C.
  2. extractionThe reaction mixture was extracted with water and dichloromethane
  3. customThe organic phase was dried on Na2SO4
  4. filtrationfiltered
  5. customthe solvent was evaporated

Sources & evidence

ORD record
ord-62aeed14c6b44e258b358674e5f33524
Source dataset
uspto-grants-2009_12
Patent number
US07629353B2

Reaction notes

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