Water → HCID 14276242, compound

HRID 1165207Notes

Reaction equation

HRID 1165207 reaction equation
[H-].[Na+].[CH2:3]([O:6][C:7]1[CH:14]=[CH:13][C:10]([CH2:11][SH:12])=[CH:9][CH:8]=1)[CH2:4][CH3:5].Cl[C:16]1[N:21]=[C:20]([S:22][CH3:23])[N:19]([CH2:24][CH3:25])[C:18](=[O:26])[C:17]=1[CH3:27].O>CN(C)P(=O)(N(C)C)N(C)C>[CH3:27][C:17]1[C:18](=[O:26])[N:19]([CH2:24][CH3:25])[C:20]([S:22][CH3:23])=[N:21][C:16]=1[S:12][CH2:11][C:10]1[CH:9]=[CH:8][C:7]([O:6][CH2:3][CH2:4][CH3:5])=[CH:14][CH:13]=1

Participants

6

Reactant 4

HCID 962WaterHCID 24758Sodium hydrideHCID 12347047HCID 12347047, compoundHCID 15058935HCID 15058935, compound

Product 1

HCID 14276242HCID 14276242, compoundYield 52%

Reagents, catalysts & solvents 1

HCID 12679HexamethylphosphoramideSolvent

Procedure

Sodium hydride (55% in mineral oil) (0.70 g) was suspended in 20 ml of hexamethyl phosphoric triamide, and then 3.0 g of 4-propyloxybenzyl mercaptan was added thereto. The mixture was stirred for one hour at room temperature and then incorporated with 3.0 g of 6-chloro-5-methyl-2-methylthio-3-ethyl-4(3H)-pyrimidinone. After stirring at room temperature, resulting mixture was heated to 80° C. under stirring for 3 hours. The resulting solution was poured into water and then extracted with benzene. The extract was washed with an aqueous sodium hydroxide solution and then with water, dried over anhydrous sodium sulfate and freed of solvent by distillation udner reduced pressure. The oil thus obtained was purified by means of column chromatography (on silica gel, eluting with chloroform) to give 2.6 g of the intended product.

Workup

  1. stirringAfter stirring at room temperature
  2. customresulting mixture
  3. temperaturewas heated to 80° C.
  4. stirringunder stirring for 3 hours
  5. extractionextracted with benzene
  6. washThe extract was washed with an aqueous sodium hydroxide solution
  7. dry with materialwith water, dried over anhydrous sodium sulfate
  8. distillationfreed of solvent by distillation udner reduced pressure
  9. customThe oil thus obtained
  10. customwas purified by means of column chromatography (on silica gel, eluting with chloroform)

Sources & evidence

ORD record
ord-a8471887ef934bd69d165a312394feda
Source dataset
uspto-grants-1990_03
Patent number
US04908379

Reaction notes

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