Pyridine → HCID 53707787, compound

HRID 1590288Notes

Reaction equation

HRID 1590288 reaction equation
COC1C=CC(CSC2NC(C)=C(C(OCC)=O)C([C:17]3[CH:22]=[CH:21][CH:20]=[C:19]([N+:23]([O-:25])=[O:24])[CH:18]=3)N=2)=CC=1.N1C=CC=CC=1.ClC(OC(C)C)=O.[CH3:45][O:46][C:47]1[CH:52]=[CH:51][C:50]([CH2:53][S:54][C:55]2[N:56]([C:76]([O:78][CH:79]([CH3:81])[CH3:80])=[O:77])[CH:57](C3C=CC=C([N+]([O-])=O)C=3)[C:58]([C:62]([O:64][CH2:65][CH3:66])=[O:63])=[C:59]([CH3:61])[N:60]=2)=[CH:49][CH:48]=1>ClCCl>[CH3:81][CH:79]([O:78][C:76]([N:56]1[CH2:57][C:58]([C:62]([O:64][CH2:65][CH3:66])=[O:63])=[C:59]([CH3:61])[N:60]([C:17]2[CH:22]=[CH:21][CH:20]=[C:19]([N+:23]([O-:25])=[O:24])[CH:18]=2)[CH:55]1[S:54][CH2:53][C:50]1[CH:49]=[CH:48][C:47]([O:46][CH3:45])=[CH:52][CH:51]=1)=[O:77])[CH3:80]

Participants

6

Reactant 4

HCID 1049PyridineHCID 7917Isopropyl chloroformateHCID 13885858HCID 13885858, compoundHCID 14788027HCID 14788027, compound

Product 1

HCID 53707787HCID 53707787, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent4×

Procedure

A solution of 1,4-dihydro-2-[[(4-methoxyphenyl)methyl]thio]-6-methyl-4-(3-nitrophenyl)-5-pyrimidinecarboxylic acid, ethyl ester (2.0 g., 4.5 mmole) in dichloromethane (20 ml.) containing pyridine (0.71 g., 9.1 mmole) is cooled to -10° and treated dropwise with a solution of isopropyl chloroformate (0.66 g., 5.4 mmole) in dichloromethane (3 ml.). After stirring at room temperature for 16 hours, dichloromethane is added and the solution is washed with water, 1N hydrochloric acid, sodium bicarbonate, and brine. The dried solution is evaporated to give 2.6 g. of an oil. Flash chromatography using dichloromethane gives 2.3 g. of 2-[[(4-methoxyphenyl)methyl]thio]-4-methyl-6-(3-nitrophenyl)-1,5(6H)-pyrimidinedicarboxylic acid, 5-ethyl 1-(1-methylethyl) ester as an oil.

Workup

  1. temperatureis cooled to -10°
  2. washthe solution is washed with water, 1N hydrochloric acid, sodium bicarbonate, and brine
  3. customThe dried solution is evaporated
  4. customto give 2.6 g
  5. customgives 2.3 g

Sources & evidence

ORD record
ord-1ec4d270d76642a4a8ab807743b47916
Source dataset
uspto-grants-1993_04
Patent number
US05202330

Reaction notes

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