Hydrogen Bromide → 7-(2-bromoethyl)-3,4-dihydro-8-methyl-2H,6H-pyrimido[2,1-b][1,3]thiazin-6-one monohydrobromide

HRID 1493922Notes

Reaction equation

HRID 1493922 reaction equation
O[CH2:2][CH2:3][C:4]1[C:13](=[O:14])[N:12]2[C:7]([S:8][CH2:9][CH2:10][CH2:11]2)=[N:6][C:5]=1[CH3:15].[BrH:16]>C(O)(=O)C>[BrH:16].[Br:16][CH2:2][CH2:3][C:4]1[C:13](=[O:14])[N:12]2[C:7]([S:8][CH2:9][CH2:10][CH2:11]2)=[N:6][C:5]=1[CH3:15]

Participants

4

Reactant 2

HCID 260Hydrogen BromideHCID 155864613,4-dihydro-7-(2-hydroxyethyl)-8-methyl-2H,6H-pyrimido[2,1-b][1,3]thiazin-6-one

Product 1

HCID 155864667-(2-bromoethyl)-3,4-dihydro-8-methyl-2H,6H-pyrimido[2,1-b][1,3]thiazin-6-one monohydrobromideYield 100%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent2×

Procedure

A mixture of 20 parts of 3,4-dihydro-7-(2-hydroxyethyl)-8-methyl-2H,6H-pyrimido[2,1-b][1,3]thiazin-6-one, 50 parts of acetic acid and 180 parts of a hydrobromic acid solution 67% in acetic acid was stirred and heated to reflux. Stirring was continued overnight at reflux temperature. The reaction mixture was evaporated and the solid residue was triturated in 2-propanone. The product was filtered off and dried, yielding 24 parts (100%) of 7-(2-bromoethyl)-3,4-dihydro-8-methyl-2H,6H-pyrimido[2,1-b][1,3]thiazin-6-one monohydrobromide; mp. 215° C. (intermediate 168).

Workup

  1. temperatureheated to reflux
  2. stirringStirring
  3. temperatureat reflux temperature
  4. customThe reaction mixture was evaporated
  5. customthe solid residue was triturated in 2-propanone
  6. filtrationThe product was filtered off
  7. customdried

Sources & evidence

ORD record
ord-6580d1d740b04843a33ffad791acb9ca
Source dataset
uspto-grants-1991_06
Patent number
US05025014

Reaction notes

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