Methanesulfonyl chloride → Methanesulfonic acid 2-(4,6-dichloro-pyrimidin-5-yl)-propyl ester

HRID 1192429Notes

Reaction equation

HRID 1192429 reaction equation
[Cl:1][C:2]1[C:7]([CH:8]([CH3:11])[CH2:9][OH:10])=[C:6]([Cl:12])[N:5]=[CH:4][N:3]=1.[CH3:13][S:14](Cl)(=[O:16])=[O:15]>C(Cl)Cl.CN(C1C=CN=CC=1)C>[Cl:12][C:6]1[C:7]([CH:8]([CH3:11])[CH2:9][O:10][S:14]([CH3:13])(=[O:16])=[O:15])=[C:2]([Cl:1])[N:3]=[CH:4][N:5]=1

Participants

5

Reactant 2

HCID 31297Methanesulfonyl chlorideHCID 865987392-(4,6-Dichloro-pyrimidin-5-yl)-propan-1-ol

Product 1

HCID 86598740Methanesulfonic acid 2-(4,6-dichloro-pyrimidin-5-yl)-propyl esterYield 98.1%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

To a solution of 2-(4,6-Dichloro-pyrimidin-5-yl)-propan-1-ol (0.40 g, 1.93 mmol) in DCM (40 mL) were added MsCl (0.50 g, 4.36 mmol), TEA (1 mL) and catalytic amount of DMAP. The mixture was stirred at room temperature for 2 hours. The solvent was removed and the residue was subject to column chromatography, eluted by hexane/ethyl acetate (4:1) to give methanesulfonic acid 2-(4,6-dichloro-pyrimidin-5-yl)-propyl ester (0.54 g, 98%). 1H NMR (CDCl3, 400 MHz) δ 8.68 (s, 1H), 4.74 (m, 1H), 4.55 (m, 1H), 4.14 (m, 1H), 2.99 (s, 3H), 1.49 (dd, J=7.2 Hz, J=1.2 Hz, 3H).

Workup

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

Sources & evidence

ORD record
ord-dce369e6a6a8494fac022c5deb35cfd1
Source dataset
uspto-grants-2014_03
Patent number
US08680114B2

Reaction notes

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