Iodoethane → 6-[bis(2,4-dimethoxybenzyl)amino]-2-(ethylsulfanyl)-3-[4-(2,2,2-trifluoroethoxy)phenyl]pyrimidin-4(3H)-one

HRID 570713Notes

Reaction equation

[CH3:1][O:2][C:3]1[CH:41]=[C:40]([O:42][CH3:43])[CH:39]=[CH:38][C:4]=1[CH2:5][N:6]([CH2:27][C:28]1[CH:33]=[CH:32][C:31]([O:34][CH3:35])=[CH:30][C:29]=1[O:36][CH3:37])[C:7]1[NH:12][C:11](=[S:13])[N:10]([C:14]2[CH:19]=[CH:18][C:17]([O:20][CH2:21][C:22]([F:25])([F:24])[F:23])=[CH:16][CH:15]=2)[C:9](=[O:26])[CH:8]=1.C(=O)([O-])O.[Na+].I[CH2:50][CH3:51]>C(#N)C>[CH3:37][O:36][C:29]1[CH:30]=[C:31]([O:34][CH3:35])[CH:32]=[CH:33][C:28]=1[CH2:27][N:6]([CH2:5][C:4]1[CH:38]=[CH:39][C:40]([O:42][CH3:43])=[CH:41][C:3]=1[O:2][CH3:1])[C:7]1[N:12]=[C:11]([S:13][CH2:50][CH3:51])[N:10]([C:14]2[CH:19]=[CH:18][C:17]([O:20][CH2:21][C:22]([F:24])([F:23])[F:25])=[CH:16][CH:15]=2)[C:9](=[O:26])[CH:8]=1

Participants

Conditions

Temperature: 70 °C

Procedure

To a solution of 6-[bis(2,4-dimethoxybenzyl)amino]-2-thioxo-3-[4-(2,2,2-trifluoroethoxy)phenyl]-2,3-dihydropyrimidin-4(1H)-one (0.65 g) in acetonitrile (7 mL) were added 1M aqueous sodium hydrogen carbonate solution (1.05 mL) and iodoethane (0.425 mL), and the mixture was stirred at 70° C. for 2 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 (0.68 g).

Workup

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

Sources & evidence

ORD record: ord-53b86a266cde4ad7bfbc5230ce2d2c8d
Source dataset: uspto-grants-2015_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09023858B2

Reaction notes

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