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

HRID 2309512Notes

Reaction equation

HRID 2309512 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 166).

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-50b7fb9d8d36455196c1379484309fea
Source dataset
uspto-grants-1987_09
Patent number
US04695569

Reaction notes

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