Sodium Acetate → HCID 86746708, compound

HRID 1590285Notes

Reaction equation

HRID 1590285 reaction equation
[CH3:1][S:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[CH:9]=[C:10]([C:16](=O)[CH3:17])[C:11]([O:13][CH2:14][CH3:15])=[O:12].Cl.[CH3:20][O:21][C:22]1[CH:32]=[CH:31][C:25]([CH2:26][S:27][C:28](=[NH:30])[NH2:29])=[CH:24][CH:23]=1.C([O-])(=O)C.[Na+].COC1C=CC(CCSC2NC(C)=C(C(OCC)=O)C(C3C=CC=CC=3SC)N=2)=CC=1>CN(C)C=O.CCOCC>[CH3:20][O:21][C:22]1[CH:23]=[CH:24][C:25]([CH2:26][S:27][C:28]2[NH:30][C:16]([CH3:17])=[C:10]([C:11]([O:13][CH2:14][CH3:15])=[O:12])[CH:9]([C:4]3[CH:5]=[CH:6][CH:7]=[CH:8][C:3]=3[S:2][CH3:1])[N:29]=2)=[CH:31][CH:32]=1

Participants

7

Reactant 4

HCID 517045Sodium AcetateHCID 13885856(4-Methoxyphenyl)methyl carbamimidothioate--hydrogen chloride (1/1)HCID 86150148HCID 86150148, compoundHCID 86746709HCID 86746709, compound

Product 1

HCID 86746708HCID 86746708, compound

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 6228DimethylformamideSolvent

Procedure

A mixture of 2-[[2-(methylthio)phenyl]methylene]-3-oxobutanoic acid, ethyl ester (2.0 g., 7.5 mmole), S-(4-methoxybenzyl)thiopseudourea, hydrochloride (1.76 g., 7.5 mmole) and sodium acetate (0.66 g. 8.0 mmole) in dimethylformamide (10 ml.) is stirred and heated at 70° for 6 hours. The cooled mixture is diluted with ether and washed with water, sodium bicarbonate, and brine. The dried solution is evaporated to give 3.0 g. of an oil. Flash chromatography using ethyl acetate:hexanes (1:4) gives 2.13 g. of 1,4-dihydro2-[[(4-methoxybenzyl)methyl]thio]-6-methyl-4-[2-(methylthio)phenyl]-5-pyrimidinecarboxylic acid, ethyl ester as a yellow oil.

Workup

  1. temperatureheated at 70° for 6 hours
  2. washwashed with water, sodium bicarbonate, and brine
  3. customThe dried solution is evaporated
  4. customto give 3.0 g
  5. customgives 2.13 g

Sources & evidence

ORD record
ord-ab4c051bf8e04b13a2353dcb2c3d9f6e
Source dataset
uspto-grants-1993_04
Patent number
US05202330

Reaction notes

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