Pyridine → HCID 86746715, compound

HRID 1590296Notes

Reaction equation

HRID 1590296 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.N1C=CC=CC=1.[C:38](Cl)(=[O:45])[C:39]1[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=1>ClCCl>[C:38]([N:16]1[CH:15]([C:17]2[CH:22]=[CH:21][CH:20]=[C:19]([N+:23]([O-:25])=[O:24])[CH:18]=2)[C:14]([C:26]([O:28][CH2:29][CH3:30])=[O:27])=[C:13]([CH3:31])[N:12]=[C:11]1[S:10][CH2:9][C:6]1[CH:7]=[CH:8][C:3]([O:2][CH3:1])=[CH:4][CH:5]=1)(=[O:45])[C:39]1[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=1

Participants

5

Reactant 3

HCID 1049PyridineHCID 7412Benzoyl chlorideHCID 13885858HCID 13885858, compound

Product 1

HCID 86746715HCID 86746715, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent3×

Procedure

A cold solution (5°) of 2.0 g. (0.0045 mole) of 1,4-dihydro-2-[[(4-methoxyphenyl)methyl]thio]-6-methyl-4-(3-nitrophenyl)-5-pyrimidinecarboxylic acid, ethyl ester in 25 ml. of dichloromethane containing 0.72 g. (0.0091 mole) of pyridine is treated slowly with a solution of 0.76 g. (0.0054 mole) of benzoyl chloride in 3 ml. of dichloromethane. After stirring at room temperature for 16 hours, the solution is diluted with dichloromethane and washed with water, 1N hydrochloric acid, sodium bicarbonate and brine. The dried solution is evaporated to give 2.37 g. of a viscous oil which is not purified.

Workup

  1. customA cold solution (5°) of 2.0 g
  2. washwashed with water, 1N hydrochloric acid, sodium bicarbonate and brine
  3. customThe dried solution is evaporated
  4. customto give 2.37 g
  5. customof a viscous oil which is not purified

Sources & evidence

ORD record
ord-9675ce2b26ca43d38f5528adb87886dd
Source dataset
uspto-grants-1993_04
Patent number
US05202330

Reaction notes

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