Potassium Carbonate → Allyl 2-[2-chloro-5-(3,5-dimethyl-2,6-dioxo-[1,3,5]triazinan-1-yl)-4-fluorophenoxy]propionate

HRID 394439Notes

Reaction equation

C([O-])([O-])=O.[K+].[K+].Br[CH:8]([CH3:15])[C:9]([O:11][CH2:12][CH:13]=[CH2:14])=[O:10].[Cl:16][C:17]1[C:22]([OH:23])=[CH:21][C:20]([N:24]2[C:29](=[O:30])[N:28]([CH3:31])[C:27](=S)[N:26]([CH3:33])[C:25]2=[O:34])=[C:19]([F:35])[CH:18]=1>CN(C)C=O>[Cl:16][C:17]1[CH:18]=[C:19]([F:35])[C:20]([N:24]2[C:25](=[O:34])[N:26]([CH3:33])[CH2:27][N:28]([CH3:31])[C:29]2=[O:30])=[CH:21][C:22]=1[O:23][CH:8]([CH3:15])[C:9]([O:11][CH2:12][CH:13]=[CH2:14])=[O:10]

Participants

Conditions

Temperature: 20 °C

Procedure

0.37 g (2.65 mmol) of K2CO3 and 0.51 g (2.65 mmol) of rac. allyl 2-bromopropionate were added approximately at 20° C. to a solution of 0.80 g (2.52 mmol) of 3-(4-chloro-2-fluoro-5-hydroxyphenyl)-1,5-dimethyl-6-thioxo-[1,3,5]triazinane-2,4-dione in 15 ml of dimethylformamide. After the reaction mixture had been stirred for two hours at approximately 20° C., it was stirred into ice-water. The product was extracted three times with methyl tert-butyl ether. The combined organic phases were dried over magnesium sulfate and then concentrated. The crude product (1.18 g) was purified by column chromatography (mobile phase: cyclohexane/ethyl acetate=15:1). Yield: 0.88 g (81%); 1H NMR (270 MHz, in CDCl3): δ[ppm]=1.7 (d, 3H), 3.8 (s, 6H), 4.6 (m, 2H), 4.7 (q, 1H), 5.2 (d, 1H), 5.3 (d, 1H), 5.9 (m, 1H), 6.9 (d, 1H), 7.3 (d, 1H).

Workup

extractionThe product was extracted three times with methyl tert-butyl ether
dry with materialThe combined organic phases were dried over magnesium sulfate
concentrationconcentrated
customThe crude product (1.18 g) was purified by column chromatography (mobile phase: cyclohexane/ethyl acetate=15:1)

Sources & evidence

ORD record: ord-47e3ae328624462499b721e8cc85f8f7
Source dataset: uspto-grants-2003_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06602825B1

Reaction notes

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