Water → HCID 14276135, compound

HRID 1165206Notes

Reaction equation

HRID 1165206 reaction equation
[OH:1][C:2]1[N:7]=[C:6]([S:8][CH3:9])[N:5]([CH2:10][CH3:11])[C:4](=[O:12])[C:3]=1[CH3:13].[F:14][C:15]([F:32])([F:31])[C:16]1[CH:30]=[CH:29][C:19]([O:20][C:21]2[CH:28]=[CH:27][C:24]([CH2:25]Br)=[CH:23][CH:22]=2)=[CH:18][CH:17]=1.[H-].[Na+].O>CN(C)P(=O)(N(C)C)N(C)C>[CH2:10]([N:5]1[C:4](=[O:12])[C:3]([CH3:13])=[C:2]([O:1][CH2:25][C:24]2[CH:23]=[CH:22][C:21]([O:20][C:19]3[CH:29]=[CH:30][C:16]([C:15]([F:14])([F:31])[F:32])=[CH:17][CH:18]=3)=[CH:28][CH:27]=2)[N:7]=[C:6]1[S:8][CH3:9])[CH3:11]

Participants

6

Reactant 4

HCID 962WaterHCID 24758Sodium hydrideHCID 14720261HCID 14720261, compoundHCID 136197565HCID 136197565, compound

Product 1

HCID 14276135HCID 14276135, compoundYield 93.4%

Reagents, catalysts & solvents 1

HCID 12679HexamethylphosphoramideSolvent

Procedure

In 10 ml of hexamethylphosphoric triamide were dissolved 1 g of 6-hydroxy-3-ethyl-5-methyl-2-methylthio-4(3H)-pyrimidinone and 1.66 g of 4-(4'-trifluoromethylphenoxy)benzyl bromide 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 washed with water, dried over anhydrous sodium sulfate and freed of solvent by distillation under reduced pressure to give 2.1 g of crystals. The crystals were recrystallized from a mixture of hexane and ethyl ether (3:1 ) to give 0.6 g of the intended product.

Workup

  1. extractionextracted twice with 30 ml of ethyl ether
  2. washThe ethyl ether layer was washed with water
  3. dry with materialdried over anhydrous sodium sulfate
  4. distillationfreed of solvent by distillation under reduced pressure

Sources & evidence

ORD record
ord-ac763ec1f86f4e37920518fd772594b7
Source dataset
uspto-grants-1990_03
Patent number
US04908379

Reaction notes

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