Iodine chloride → 1-[2-fluoro-6-(trifluoromethyl)benzyl]-5-iodo-6-methylpyrimidine-2,4(1H,3H)-dione

HRID 1049105Notes

Reaction equation

[F:1][C:2]1[CH:17]=[CH:16][CH:15]=[C:14]([C:18]([F:21])([F:20])[F:19])[C:3]=1[CH2:4][N:5]1[C:10]([CH3:11])=[CH:9][C:8](=[O:12])[NH:7][C:6]1=[O:13].[I:22]Cl>CO>[F:1][C:2]1[CH:17]=[CH:16][CH:15]=[C:14]([C:18]([F:21])([F:19])[F:20])[C:3]=1[CH2:4][N:5]1[C:10]([CH3:11])=[C:9]([I:22])[C:8](=[O:12])[NH:7][C:6]1=[O:13]

Participants

Conditions

Temperature: 50 °C

Procedure

To a 250 mL three-neck round bottom flask was charged 1-(2-fluoro-6-trifluoromethyl-benzyl)-6-methyl-1H-pyrimidine-2,4-dione 1a (25.0 g) and methanol (250 mL). Iodine monochloride (30.9 g) was charged over 2.5 min. The mixture was heated at 50° C. for 3 hours. After cooling to ambient temperature, the mixture was filtered. The cake was re-slurried in methanol (250 mL) and heated to 50° C. for 3 hours. After cooling to ambient temperature, the mixture was filtered and the filter cake was washed with methanol (50 mL). The off-white solid was dried in a vacuum oven at 50° C. to provide 1-(2-fluoro-6-trifluoromethyl-benzyl)-5-iodo-6-methyl-1H-pyrimidine-2,4-dione 1b (32.5 g, 90% yield). LCMS (ESI) m/z 429.3 (MH+). The material may be re-slurried in MeOH as needed.

Workup

temperatureAfter cooling to ambient temperature
filtrationthe mixture was filtered
temperatureheated to 50° C. for 3 hours
temperatureAfter cooling to ambient temperature
filtrationthe mixture was filtered
washthe filter cake was washed with methanol (50 mL)
customThe off-white solid was dried in a vacuum oven at 50° C.

Sources & evidence

ORD record: ord-0fa7d23757ba427981e58956b651e93b
Source dataset: uspto-grants-2016_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09382214B2

Reaction notes

Loading…