Epibromohydrin → 3-Oxiranylmethyl-6,7,8,9-tetrahydropyrido[1,2-a][1,3,5]triazine-2,4-dione

HRID 889163Notes

Reaction equation

HRID 889163 reaction equation
[N:1]1[C:6](=[O:7])[NH:5][C:4](=[O:8])[N:3]2[CH2:9][CH2:10][CH2:11][CH2:12][C:2]=12.[CH2:13]([CH:15]1[O:17][CH2:16]1)Br.[H-].[Na+]>CN(C)C=O>[O:17]1[CH2:16][CH:15]1[CH2:13][N:5]1[C:4](=[O:8])[N:3]2[CH2:9][CH2:10][CH2:11][CH2:12][C:2]2=[N:1][C:6]1=[O:7]

Participants

5

Reactant 3

HCID 18430EpibromohydrinHCID 24758Sodium hydrideHCID 151053696,7,8,9-Tetrahydropyrido[1,2-a][1,3,5]triazine-2,4-dione

Product 1

HCID 579275773-Oxiranylmethyl-6,7,8,9-tetrahydropyrido[1,2-a][1,3,5]triazine-2,4-dioneYield 72.6%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

After dissolving 6,7,8,9-tetrahydropyrido[1,2-a][1,3,5]triazine-2,4-dione (CAS 133365-43-2) (195 mg) and epibromohydrin (321 mg) in N,N-dimethylformamide (1 ml), sodium hydride (60% in oil) (52 mg) was added and the mixture was stirred overnight at room temperature. The reaction mixture was concentrated under reduced pressure, and the residue was purified by NH silica gel column chromatography. The title compound (189 mg) was thus obtained.

Workup

  1. additionwas added
  2. concentrationThe reaction mixture was concentrated under reduced pressure
  3. customthe residue was purified by NH silica gel column chromatography

Sources & evidence

ORD record
ord-92e18b9edffd487bbe04b593b258b6b6
Source dataset
uspto-grants-2012_08
Patent number
US08252810B2

Reaction notes

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