Sodium Bicarbonate → HCID 18519616, compound

HRID 1368020Notes

Reaction equation

[NH2:1][C:2]1[C:7]([OH:8])=[C:6]([Cl:9])[CH:5]=[C:4]([F:10])[C:3]=1[N:11]1[C:16](=[O:17])[CH:15]=[C:14]([C:18]([F:21])([F:20])[F:19])[N:13]([CH3:22])[C:12]1=[O:23].Br[CH2:25]/[CH:26]=[CH:27]/[C:28]([O:30][CH3:31])=[O:29].C(=O)(O)[O-].[Na+]>CO>[Cl:9][C:6]1[C:7]2[O:8][CH:26]([CH2:27][C:28]([O:30][CH3:31])=[O:29])[CH2:25][NH:1][C:2]=2[C:3]([N:11]2[C:16](=[O:17])[CH:15]=[C:14]([C:18]([F:21])([F:20])[F:19])[N:13]([CH3:22])[C:12]2=[O:23])=[C:4]([F:10])[CH:5]=1

Participants

Conditions

Temperature: 25 °C

Procedure

A mixture of 3-(2-amino-4-chloro-6-fluoro-3-hydroxyphenyl)-1-methyl-6-trifluoromethyl-2,4(1H,3H)-pyrimidinedione (0.43 g), methyl 4-bromocrotonate (0.22 g ) and sodium bicarbonate (0.3 g ) in methanol was stirred at 25° C. for 12 hours . The solvent was removed under reduced pressure and ethyl acetate (200 ml) was added. The organic phase was washed with saturated brine, dried over anhydrous sodium sulfate and concentrated to an oil. The crude product was purified by column chromatography on silica gel using ethyl acetate-hexane (1:2) as eluent to give title compounds (0.097 g)

Workup

customThe solvent was removed under reduced pressure and ethyl acetate (200 ml)
additionwas added
washThe organic phase was washed with saturated brine
dry with materialdried over anhydrous sodium sulfate
concentrationconcentrated to an oil
customThe crude product was purified by column chromatography on silica gel

Sources & evidence

ORD record: ord-b4a5117634494349ab41b0293569b8ca
Source dataset: uspto-grants-2003_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06573218B1

Reaction notes

Loading…