Triethylamine → Methanesulfonic acid 2-(4,6-dichloro-pyrimidin-5-yl)-ethyl ester

HRID 1192424Notes

Reaction equation

HRID 1192424 reaction equation
[Cl:1][C:2]1[C:7]([CH2:8][CH2:9][OH:10])=[C:6]([Cl:11])[N:5]=[CH:4][N:3]=1.[CH3:12][S:13](Cl)(=[O:15])=[O:14].C(N(CC)CC)C>C(Cl)Cl.CN(C1C=CN=CC=1)C>[Cl:11][C:6]1[C:7]([CH2:8][CH2:9][O:10][S:13]([CH3:12])(=[O:15])=[O:14])=[C:2]([Cl:1])[N:3]=[CH:4][N:5]=1

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 529881462-(4,6-Dichloropyrimidin-5-yl)ethan-1-ol

Product 1

HCID 86598737Methanesulfonic acid 2-(4,6-dichloro-pyrimidin-5-yl)-ethyl esterYield 80%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

To a solution of 2-(4,6-Dichloro-pyrimidin-5-yl)-ethanol (0.46 g, 2.4 mmol) in DCM (40 mL) and was added MsCl (0.50 g, 4.36 mmol), triethylamine (1 mL) and cat. amount of DMAP. After stirring at room temperature overnight, the solvent was removed and the residue was subject to column chromatography, eluted by hexane/ethyl acetate (4:1) to afford methanesulfonic acid 2-(4,6-dichloro-pyrimidin-5-yl)-ethyl ester (0.52 g, 80%). 1H NMR (CDCl3, 400 MHz) δ 8.71 (s, 1H), 4.50 (t, J=6.4 Hz, 2H), 3.42 (t, J=6.8 Hz, 2H), 3.02 (s, 3H).

Workup

  1. customthe solvent was removed
  2. washeluted by hexane/ethyl acetate (4:1)

Sources & evidence

ORD record
ord-4b908bea90174ec1963f181766130879
Source dataset
uspto-grants-2014_03
Patent number
US08680114B2

Reaction notes

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