Pyridine → HCID 14788028, compound

HRID 1590293Notes

Reaction equation

HRID 1590293 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([CH2:9][S:10][C:11]2[NH:12][C:13]([CH3:31])=[C:14]([C:26]([O:28][CH2:29][CH3:30])=[O:27])[CH:15]([C:17]3[CH:22]=[CH:21][CH:20]=[C:19]([N+:23]([O-:25])=[O:24])[CH:18]=3)[N:16]=2)=[CH:5][CH:4]=1.ClCCl.N1C=CC=CC=1.[C:41](Cl)(=[O:50])[C:42]1[CH:47]=[CH:46][C:45]([O:48][CH3:49])=[CH:44][CH:43]=1>C(OCC)(=O)C.CCCCCC>[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([CH2:9][S:10][C:11]2[N:16]([C:41]([C:42]3[CH:47]=[CH:46][C:45]([O:48][CH3:49])=[CH:44][CH:43]=3)=[O:50])[CH:15]([C:17]3[CH:22]=[CH:21][CH:20]=[C:19]([N+:23]([O-:25])=[O:24])[CH:18]=3)[C:14]([C:26]([O:28][CH2:29][CH3:30])=[O:27])=[C:13]([CH3:31])[N:12]=2)=[CH:5][CH:4]=1

Participants

6

Reactant 4

HCID 1049PyridineHCID 6344Dichloromethane3×HCID 7477p-Anisoyl chlorideHCID 13885858HCID 13885858, compound

Product 1

HCID 14788028HCID 14788028, compound

Reagents, catalysts & solvents 1

HCID 21226206Ethyl acetate hexaneSolvent

Procedure

A solution of 1.5 g. (0.0034 mole) of 1,4-dihydro-2-[[(4-methoxyphenyl)methyl]thio]-6-methyl-4-(3-nitrophenyl)-5-pyrimidinecarboxylic acid, ethyl ester in 10 ml. of dichloromethane containing 0.6 ml. (0.0074 mole) of pyridine is treated gradually with a solution of 0.70 g (0.0041 mole) of p-anisoyl chloride in 10 ml. of dichloromethane. After stirring for 16 hours at room temperature, dichloromethane is added and the solution is washed with water, 1N hydrochloric acid, sodium bicarbonate and brine. The dried solution is evaporated to give 1.8 g. of an impure oil. Flash chromatography using ethyl acetate/hexane (1:3) gives 1.58 g. of yellow oil.

Workup

  1. washthe solution is washed with water, 1N hydrochloric acid, sodium bicarbonate and brine
  2. customThe dried solution is evaporated
  3. customto give 1.8 g
  4. customgives 1.58 g

Sources & evidence

ORD record
ord-a7f1aecde591460898082ab5f164c258
Source dataset
uspto-grants-1993_04
Patent number
US05202330

Reaction notes

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