Pyridine → HCID 14788018, compound

HRID 1590287Notes

Reaction equation

HRID 1590287 reaction equation
N1C=CC=C[CH:2]=1.ClC(OCC)=O.[CH3:13][O:14][C:15]1[CH:20]=[CH:19][C:18]([CH2:21][S:22][C:23]2[N:24]([C:41]([O:43][CH2:44][CH3:45])=[O:42])[CH:25]([C:34]3[CH:39]=[CH:38][CH:37]=[C:36]([Cl:40])[CH:35]=3)[C:26]([C:29]([O:31][CH2:32][CH3:33])=[O:30])=[CH:27][N:28]=2)=[CH:17][CH:16]=1>ClCCl.CCOCC>[CH3:13][O:14][C:15]1[CH:20]=[CH:19][C:18]([CH2:21][S:22][C:23]2[N:24]([C:41]([O:43][CH2:44][CH3:45])=[O:42])[CH:25]([C:34]3[CH:39]=[CH:38][CH:37]=[C:36]([Cl:40])[CH:35]=3)[C:26]([C:29]([O:31][CH2:32][CH3:33])=[O:30])=[C:27]([CH3:2])[N:28]=2)=[CH:17][CH:16]=1

Participants

6

Reactant 3

HCID 1049PyridineHCID 10928Ethyl chloroformateHCID 86746710HCID 86746710, compound

Product 1

HCID 14788018HCID 14788018, compound

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 6344DichloromethaneSolvent

Procedure

A cold solution of the ethyl ester product from part (a) (2.0 g., 4.6 mmole) and pyridine (0.76 ml., 9.3 mmole) in dichloromethane (15 ml.) is treated dropwise with ethyl chloroformate (0.48 g., 4.4 mmole) and stirred at room temperature for 24 hours. The solution is diluted with ether and washed with water, 1N hydrochloric acid, sodium bicarbonate, and brine. The dried solution is evaporated to give 1.87 g. of 2-[[(4-methoxyphenyl)methyl]thio]-6-(3-chlorophenyl)-1,5(6H)-pyrimidinedicarboxylic acid, diethyl ester as an oil.

Workup

  1. washwashed with water, 1N hydrochloric acid, sodium bicarbonate, and brine
  2. customThe dried solution is evaporated
  3. customto give 1.87 g

Sources & evidence

ORD record
ord-939ef4675f614d439829545c17b7860f
Source dataset
uspto-grants-1993_04
Patent number
US05202330

Reaction notes

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