Pyridine → HCID 86746711, compound

HRID 1590291Notes

Reaction equation

HRID 1590291 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]([CH3:30])=[C:14]([C:26]([O:28][CH3:29])=[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.[C:31](Cl)(=[O:34])[CH2:32][CH3:33].N1C=CC=CC=1>ClCCl.CCOCC>[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([CH2:9][S:10][C:11]2[N:16]([C:31](=[O:34])[CH2:32][CH3:33])[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][CH3:29])=[O:27])=[C:13]([CH3:30])[N:12]=2)=[CH:5][CH:4]=1

Participants

6

Reactant 3

HCID 1049PyridineHCID 62324Propionyl chlorideHCID 13885857HCID 13885857, compound

Product 1

HCID 86746711HCID 86746711, compound

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 6344DichloromethaneSolvent

Procedure

1,4-Dihydro-2-[[(4-methoxyphenyl)methyl]thio]-6-methyl-4-(3-nitrophenyl)-5-pyrimidinecarboxylic acid, methyl ester (1.52 g., 3.5 mmole) in 15 ml of dichloromethane is cooled under argon to 0°-5° C. and treated with propionyl chloride (0.43 g., 4.7 mmole) and pyridine (0.55 g., 7.0 mmole). The mixture is then allowed to stir at room temperature for 3 hours, diluted with ether and the salt is filtered. The filtrate is washed with water, 1N hydrochloric acid, water, aqueous sodium bicarbonate, water and saturated brine. The aqueous fractions are back extracted with fresh ether. The combined organic solutions are dried (magnesium sulfate) and concentrated in vacuo to give 1.6 g. of a viscous oily product.

Workup

  1. filtrationthe salt is filtered
  2. washThe filtrate is washed with water, 1N hydrochloric acid, water, aqueous sodium bicarbonate, water and saturated brine
  3. extractionThe aqueous fractions are back extracted with fresh ether
  4. dry with materialThe combined organic solutions are dried (magnesium sulfate)
  5. concentrationconcentrated in vacuo
  6. customto give 1.6 g

Sources & evidence

ORD record
ord-2ddcd9ee5ee949beb68bc6b0e5991dc2
Source dataset
uspto-grants-1993_04
Patent number
US05202330

Reaction notes

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