Trifluoroacetic acid → 6-amino-2-(ethylsulfanyl)-3-[4-(2,2,2-trifluoroethoxy)phenyl]pyrimidin-4(3H)-one

HRID 570714Notes

Reaction equation

HRID 570714 reaction equation
COC1C=C(OC)C=CC=1C[N:6](CC1C=CC(OC)=CC=1OC)[C:7]1[N:12]=[C:11]([S:13][CH2:14][CH3:15])[N:10]([C:16]2[CH:21]=[CH:20][C:19]([O:22][CH2:23][C:24]([F:27])([F:26])[F:25])=[CH:18][CH:17]=2)[C:9](=[O:28])[CH:8]=1.C1(OC)C=CC=CC=1.FC(F)(F)C(O)=O>>[NH2:6][C:7]1[N:12]=[C:11]([S:13][CH2:14][CH3:15])[N:10]([C:16]2[CH:17]=[CH:18][C:19]([O:22][CH2:23][C:24]([F:26])([F:27])[F:25])=[CH:20][CH:21]=2)[C:9](=[O:28])[CH:8]=1

Participants

4

Reactant 3

HCID 6422Trifluoroacetic acidHCID 7519AnisoleHCID 866853736-[bis(2,4-dimethoxybenzyl)amino]-2-(ethylsulfanyl)-3-[4-(2,2,2-trifluoroethoxy)phenyl]pyrimidin-4(3H)-one

Product 1

HCID 866853746-amino-2-(ethylsulfanyl)-3-[4-(2,2,2-trifluoroethoxy)phenyl]pyrimidin-4(3H)-oneYield 52.2%

Procedure

A mixture of 6-[bis(2,4-dimethoxybenzyl)amino]-2-(ethylsulfanyl)-3-[4-(2,2,2-trifluoroethoxy)phenyl]pyrimidin-4(3H)-one (0.68 g), anisole (0.459 mL) and trifluoroacetic acid (7 mL) was stirred at room temperature for 1 hr. The solvent was evaporated under reduced pressure, and the residue was purified by silica gel column chromatography (ethyl acetate/hexane) to give the title compound (0.19 g).

Workup

  1. customThe solvent was evaporated under reduced pressure
  2. customthe residue was purified by silica gel column chromatography (ethyl acetate/hexane)

Sources & evidence

ORD record
ord-6718514f11f34fa5b984472ce169d9e7
Source dataset
uspto-grants-2015_05
Patent number
US09023858B2

Reaction notes

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