Triethylamine → 5-Methanesulfonyloxy-pyrazine-2-carboxylic acid methyl ester

HRID 639308Notes

Reaction equation

HRID 639308 reaction equation
[OH:1][C:2]1[N:3]=[CH:4][C:5]([C:8]([O:10][CH3:11])=[O:9])=[N:6][CH:7]=1.[CH3:12][S:13](Cl)(=[O:15])=[O:14].CCN(CC)CC.C([O-])([O-])=O.[Na+].[Na+]>C(Cl)Cl.O>[CH3:11][O:10][C:8]([C:5]1[CH:4]=[N:3][C:2]([O:1][S:13]([CH3:12])(=[O:15])=[O:14])=[CH:7][N:6]=1)=[O:9]

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 10340Sodium CarbonateHCID 31297Methanesulfonyl chlorideHCID 178498852HCID 178498852, compound

Product 1

HCID 866195215-Methanesulfonyloxy-pyrazine-2-carboxylic acid methyl esterYield 73%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

A mixture of 3.34 g (22 mmol) methyl 5-hydroxypyrazine-2-carboxylate (commercially available), 2.73 g (24 mmol) methane sulfonyl chloride and 3.29 g (33 mmol) NEt3 in 40 mL DCM was stirred at room temperature for 4 h. Water and Na2CO3 was added and the organic layer was separated and dried with MgSO4. Evaporation yielded 3.7 g (73%) of the title compound which was used without further purification. 300-MHz-1H-NMR (DMSO): δ=9.06 (d, J=1.2 Hz, 1H, 3-H), 8.83 (d, J=1.2 Hz, 1H, 6-H), d=3.97 (s, 3H, OMe), 3.74 (s, 3H, SO2Me).

Workup

  1. customthe organic layer was separated
  2. dry with materialdried with MgSO4
  3. customEvaporation

Sources & evidence

ORD record
ord-a28d5d06505e476a93e6d40f5d7a8997
Source dataset
uspto-grants-2010_04
Patent number
US07691863B2

Reaction notes

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