Water → HCID 14276134, compound

HRID 1165205Notes

Reaction equation

HRID 1165205 reaction equation
[CH3:1][N:2]1[C:7](=[O:8])[C:6]([CH3:9])=[C:5]([OH:10])[N:4]=[C:3]1[S:11][CH3:12].[C:13]([C:17]1[CH:24]=[CH:23][C:20]([CH2:21]Cl)=[CH:19][CH:18]=1)([CH3:16])([CH3:15])[CH3:14].[H-].[Na+].O>CN(C)P(=O)(N(C)C)N(C)C>[C:13]([C:17]1[CH:18]=[CH:19][C:20]([CH2:21][O:10][C:5]2[N:4]=[C:3]([S:11][CH3:12])[N:2]([CH3:1])[C:7](=[O:8])[C:6]=2[CH3:9])=[CH:23][CH:24]=1)([CH3:16])([CH3:14])[CH3:15]

Participants

6

Reactant 4

HCID 962WaterHCID 24758Sodium hydrideHCID 88198Benzene, 1-(chloromethyl)-4-(1,1-dimethylethyl)-HCID 136183857HCID 136183857, compound

Product 1

HCID 14276134HCID 14276134, compoundYield 44.8%

Reagents, catalysts & solvents 1

HCID 12679HexamethylphosphoramideSolvent

Procedure

In 10 ml of hexamethyl phosphoric triamide were dissolved 1 g of 3,5-dimethyl-6-hydroxy-2-methylthio-4(3H)-pyrimidinone and 1 g of 4-t-butylbenzyl chloride, and thereto was added 0.3 g of sodium hydride (55% in mineral oil). The mixture was stirred for 15 hours at room temperature. The resulting solution was poured into 50 ml of water and then extracted twice with 30 ml of ethyl ether. The ethyl ether layer was dried over anhydrous sodium sulfate and freed of solvent by distillation under reduced pressure to give 1.9 g of a crude product. The product was purified by means of column chromatography (on silica gel, eluting with benzene) and then washed with a mixture of hexane and ethyl ether (10:1) to give 0.8 g of the intended product.

Workup

  1. extractionextracted twice with 30 ml of ethyl ether
  2. dry with materialThe ethyl ether layer was dried over anhydrous sodium sulfate
  3. distillationfreed of solvent by distillation under reduced pressure
  4. customto give 1.9 g of a crude product
  5. customThe product was purified by means of column chromatography (on silica gel, eluting with benzene)
  6. washwashed with a mixture of hexane and ethyl ether (10:1)

Sources & evidence

ORD record
ord-8467682d1e844cfc9ebf759b900b1665
Source dataset
uspto-grants-1990_03
Patent number
US04908379

Reaction notes

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