Triethylamine → 3-(2-methanesulfonyloxyethyl)-6,7,8,9-tetrahydro-2H-pyrido[1,2-a]-1,3,5-triazine-2,4(3H)-dione

HRID 2253681Notes

Reaction equation

HRID 2253681 reaction equation
[OH:1][CH2:2][CH2:3][N:4]1[C:9](=[O:10])[N:8]2[CH2:11][CH2:12][CH2:13][CH2:14][C:7]2=[N:6][C:5]1=[O:15].C(N(CC)CC)C.[CH3:23][S:24](Cl)(=[O:26])=[O:25]>C(#N)C>[CH3:23][S:24]([O:1][CH2:2][CH2:3][N:4]1[C:9](=[O:10])[N:8]2[CH2:11][CH2:12][CH2:13][CH2:14][C:7]2=[N:6][C:5]1=[O:15])(=[O:26])=[O:25]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 197460343-(2-hydroxyethyl)-6,7,8,9-tetrahydro-2H-pyrido[1,2-a]-1,3,5-triazine-2,4(3H)-dione

Product 1

HCID 197459873-(2-methanesulfonyloxyethyl)-6,7,8,9-tetrahydro-2H-pyrido[1,2-a]-1,3,5-triazine-2,4(3H)-dioneYield 94.9%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To an ice-cooled solution of 1.80 g of 3-(2-hydroxyethyl)-6,7,8,9-tetrahydro-2H-pyrido[1,2-a]-1,3,5-triazine-2,4(3H)-dione prepared in Reference Example 27 and 1.20 g of triethylamine in 25 ml of acetonitrile, 1.17 g of methanesufonyl chloride was added dropwise. After stirring for 30 minutes, the mixture was concentrated to dryness, and the residue was extracted with chloroform. Concentration of the chloroform solution gave 2.34 g of the entitled compound as an yellow oil.

Workup

  1. additionwas added dropwise
  2. concentrationthe mixture was concentrated to dryness
  3. extractionthe residue was extracted with chloroform

Sources & evidence

ORD record
ord-460309cbeac7415caac181a0583197c1
Source dataset
uspto-grants-1993_08
Patent number
US05232924

Reaction notes

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