Ethyl Acetate → Methanesulfonic acid 2-(7-methyl-5-oxo-2,3-dihydro-5H-thiazolo[3,2-a]pyrimidin-6-yl)ethyl ester

HRID 889167Notes

Reaction equation

HRID 889167 reaction equation
[OH:1][CH2:2][CH2:3][C:4]1[C:9](=[O:10])[N:8]2[CH2:11][CH2:12][S:13][C:7]2=[N:6][C:5]=1[CH3:14].[CH3:15][S:16](Cl)(=[O:18])=[O:17].C(OCC)(=O)C>ClCCl.C(N(CC)CC)C>[CH3:14][C:5]1[N:6]=[C:7]2[S:13][CH2:12][CH2:11][N:8]2[C:9](=[O:10])[C:4]=1[CH2:3][CH2:2][O:1][S:16]([CH3:15])(=[O:18])=[O:17]

Participants

6

Reactant 3

HCID 8857Ethyl AcetateHCID 31297Methanesulfonyl chlorideHCID 155864626-(2-Hydroxyethyl)-7-methyl-2H-thiazolo[3,2-a]pyrimidin-5(3H)-one

Product 1

HCID 57927389Methanesulfonic acid 2-(7-methyl-5-oxo-2,3-dihydro-5H-thiazolo[3,2-a]pyrimidin-6-yl)ethyl ester

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8471TriethylamineSolvent

Procedure

After dissolving 6-(2-hydroxy-ethyl)-7-methyl-2,3-dihydro-thiazolo[3,2-a]pyrimidin-5-one (CAS 86487-53-8) (225 mg) in dichloromethane (10 ml), triethylamine (0.44 ml) was added, and then methanesulfonyl chloride (0.20 ml) was added dropwise while stirring on ice. After stirring for 10 minutes, ethyl acetate was added to the reaction mixture and the resulting mixture was filtered. The filtrate was concentrated under reduced pressure, and the residue was purified by NH silica gel column chromatography to obtain the title compound (264 mg).

Workup

  1. additionwas added
  2. stirringAfter stirring for 10 minutes
  3. filtrationthe resulting mixture was filtered
  4. concentrationThe filtrate was concentrated under reduced pressure
  5. customthe residue was purified by NH silica gel column chromatography

Sources & evidence

ORD record
ord-e16b8c97a0214aca9f38d5e16e02f18b
Source dataset
uspto-grants-2012_08
Patent number
US08252810B2

Reaction notes

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