Lawesson's reagent → HCID 22466474, compound

HRID 1934323Notes

Reaction equation

HRID 1934323 reaction equation
[Cl:1][C:2]1[S:18][C:5]2[N:6]=[C:7]([O:14][CH2:15][CH2:16][CH3:17])[N:8]([CH2:11][CH2:12][CH3:13])[C:9](=O)[C:4]=2[CH:3]=1.COC1C=CC(P2(SP(C3C=CC(OC)=CC=3)(=S)S2)=[S:28])=CC=1>O1CCOCC1>[Cl:1][C:2]1[S:18][C:5]2[N:6]=[C:7]([O:14][CH2:15][CH2:16][CH3:17])[N:8]([CH2:11][CH2:12][CH3:13])[C:9](=[S:28])[C:4]=2[CH:3]=1

Participants

4

Reactant 2

HCID 87949Lawesson's reagentHCID 224664756-Chloro-2-propoxy-3-propylthieno[2,3-d]pyrimidin-4(3H)-one

Product 1

HCID 22466474HCID 22466474, compound

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

In a sulfonation flask, a mixture of 1.15 g 6-chloro-2-propoxy-3-propyl-4-oxo-thieno[2,3-d]pyrimidine, 0.97g Lawesson reagent and 50 ml of dioxane is heated at reflux temperature for 3.5 hours. After removal of the solvent in the water jet vacuum, the residue is taken up in ethylacetate and the organic phase is washed twice with water. The organic phase is dried over sodium sulfate and the solvent removed in the water jet vacuum. The crude material is purified twice by column chromatography over silica gel (eluant: tert. butylmethylether/hexane 1:9). Yield: 0.3 g pure 6-chloro-2-propoxy-3-propyl-4thioxo-thieno[2,3-d]pyrimidine in the form of a yellow powder; m.p. 81-83° C.

Workup

  1. temperatureis heated
  2. temperatureat reflux temperature for 3.5 hours
  3. customAfter removal of the solvent in the water jet vacuum
  4. washthe organic phase is washed twice with water
  5. dry with materialThe organic phase is dried over sodium sulfate
  6. customthe solvent removed in the water jet vacuum
  7. customThe crude material is purified twice by column chromatography over silica gel (eluant: tert. butylmethylether/hexane 1:9)

Sources & evidence

ORD record
ord-03cab8804c8f4ad680718685cd8a43bb
Source dataset
uspto-grants-2002_05
Patent number
US06384040B1

Reaction notes

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