Ethanethiol → HCID 86746712, compound

HRID 1590292Notes

Reaction equation

HRID 1590292 reaction equation
COC1C=CC(C[S:10][C:11]2[N:12]([C:31](=[O:34])[CH2:32][CH3:33])[CH:13]([C:22]3[CH:27]=[CH:26][CH:25]=[C:24]([N+:28]([O-:30])=[O:29])[CH:23]=3)[C:14]([C:18]([O:20][CH3:21])=[O:19])=[C:15]([CH3:17])[N:16]=2)=CC=1.FC(F)(F)C(O)=O.C(S)C.C(OCC)(=O)C>ClCCl>[CH3:17][C:15]1[NH:16][C:11](=[S:10])[N:12]([C:31](=[O:34])[CH2:32][CH3:33])[CH:13]([C:22]2[CH:27]=[CH:26][CH:25]=[C:24]([N+:28]([O-:30])=[O:29])[CH:23]=2)[C:14]=1[C:18]([O:20][CH3:21])=[O:19]

Participants

6

Reactant 4

HCID 6343EthanethiolHCID 6422Trifluoroacetic acidHCID 8857Ethyl AcetateHCID 86746711HCID 86746711, compound

Product 1

HCID 86746712HCID 86746712, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

1,6-Dihydro-2-[[(4-methoxyphenyl)methyl]thio]-4-methyl-6-(3-nitrophenyl)-1-(1-oxopropyl)-5-pyrimidinecarboxylic acid, methyl ester (1.6 g., 3.3 mmole) in 20 ml of dichloromethane under argon at room temperature is treated with trifluoroacetic acid (0.75 ml., 1.1 g., 9.7 mmole) and ethanethiol (0.4 ml, 0.33 g, 5.4 mmole). After 3 hours, volatiles are evaporated in vacuo and the residue (solidified) is triturated with isopropyl ether to give 0.95 g. of product, m.p. 167°-171°. TLC(silica gel; ethyl acetate:hexanes, 1:1) Rf =0.50.

Workup

  1. customvolatiles are evaporated in vacuo
  2. customthe residue (solidified) is triturated with isopropyl ether
  3. customto give 0.95 g

Sources & evidence

ORD record
ord-4cd3f3c5afcf4e46b0c33015ab22b2f0
Source dataset
uspto-grants-1993_04
Patent number
US05202330

Reaction notes

Loading…