Water → HCID 88545615, compound

HRID 1510823Notes

Reaction equation

[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:13](/[CH:14]=[CH:15]/[C:16]([OH:18])=[O:17])=[C:12]([CH:19]([CH3:21])[CH3:20])[N:11]=[C:10]([N:22]([CH3:27])[S:23]([CH3:26])(=[O:25])=[O:24])[N:9]=2)=[CH:4][CH:3]=1.C(N(CC)CC)C.Cl[C:36]([O:38][CH3:39])=[O:37].O>C(Cl)Cl>[C:36](=[O:37])([O:38][CH3:39])[O:17][C:16](=[O:18])/[CH:15]=[CH:14]/[C:13]1[C:8]([C:5]2[CH:6]=[CH:7][C:2]([F:1])=[CH:3][CH:4]=2)=[N:9][C:10]([N:22]([CH3:27])[S:23]([CH3:26])(=[O:25])=[O:24])=[N:11][C:12]=1[CH:19]([CH3:20])[CH3:21]

Participants

Conditions

Temperature: 0 °C

Procedure

3-[4-(4-Fluorophenyl)-6-isopropyl-2-(N-methyl-N-methylsulfonylamino)pyrimidin-5-yl](2E)-propenoic acid (5 g, 0.012 m) was dissolved in methylene chloride (25 ml) and triethylamine (1.54 g, 0.015 m) was added at 25° C. The mixture was cooled to 0° C. and methyl chloroformate (1.31 g, 0.013 m) was added to the reaction mass slowly over a period of 10 min keeping the temperature below 5° C. The reaction mixture was stirred at 0-5° C. for 30 min and water (25 ml) was added to it. The organic layer was separated and washed with aqueous sodium bicarbonate solution (5% w/v, 20 ml) followed by water (20 ml). Methylene chloride was distilled out under reduced pressure at 40-45° C. to obtain the product as an oily mass, which was crystallized from n-hexane to obtain while crystalline solid (Yield: 5.4 g, 98%).

Workup

customthe temperature below 5° C
customThe organic layer was separated
washwashed with aqueous sodium bicarbonate solution (5% w/v, 20 ml)
distillationMethylene chloride was distilled out under reduced pressure at 40-45° C.
customto obtain the product as an oily mass, which
customwas crystallized from n-hexane

Sources & evidence

ORD record: ord-c77ae399f84e46e69cd737aa06721e17
Source dataset: uspto-grants-2012_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08212034B2

Reaction notes

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