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

HRID 325915Notes

Reaction equation

HRID 325915 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 rises 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 8).

Workup

  1. customrises 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-3940c8c1559344158165909f0462b558
Source dataset
uspto-grants-1984_04
Patent number
US04443451

Reaction notes

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