1,3-Dibromopropane → 3,4-dihydro-7-(2-hydroxyethyl)-8-methyl-2H,6H-pyrimido[2,1-b][1,3]thiazin-6-one

HRID 1381864Notes

Reaction equation

HRID 1381864 reaction equation
[OH:1][C:2]1[C:7]([CH2:8][CH2:9][OH:10])=[C:6]([CH3:11])[N:5]=[C:4]([SH:12])[N:3]=1.C(=O)([O-])[O-].[K+].[K+].CN(C)C(=O)C.Br[CH2:26][CH2:27][CH2:28]Br>O>[OH:10][CH2:9][CH2:8][C:7]1[C:2](=[O:1])[N:3]2[C:4]([S:12][CH2:26][CH2:27][CH2:28]2)=[N:5][C:6]=1[CH3:11]

Participants

6

Reactant 4

HCID 80011,3-DibromopropaneHCID 11430Potassium CarbonateHCID 31374DimethylacetamideHCID 178433550HCID 178433550, compound

Product 1

HCID 155864613,4-dihydro-7-(2-hydroxyethyl)-8-methyl-2H,6H-pyrimido[2,1-b][1,3]thiazin-6-oneYield 58%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 30 parts of 4-hydroxy-2-mercapto-6-methyl-5-pyrimidineethanol, 25 parts of potassium carbonate, 270 parts of N,N-dimethylacetamide and 75 parts of water was stirred at room temperature and 36 parts of 1,3-dibromopropane were added at once: temperature rose to 50° C. The whole was stirred overnight at room temperature. The reaction mixture was evaporated and water was added to the residue. The solid product was washed with water and dried in vacuo at 100° C., yielding 21 parts (58%) of 3,4-dihydro-7-(2-hydroxyethyl)-8-methyl-2H,6H-pyrimido-[2,1-b][1,3]thiazin-6-one; mp. 155° C. (intermediate 6).

Workup

  1. customrose to 50° C
  2. stirringThe whole was stirred overnight at room temperature
  3. customThe reaction mixture was evaporated
  4. additionwater was added to the residue
  5. washThe solid product was washed with water
  6. customdried in vacuo at 100° C.

Sources & evidence

ORD record
ord-99bb38a3ba2f425681301f17215b7fcd
Source dataset
uspto-grants-1989_02
Patent number
US04804663

Reaction notes

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