تفاعل #1328452

ord-8f298e889c5f419a886f1c17c476cfd5

معادلة التفاعل

COC(=O)COc1ncccc1Oc1cc(-n2c(=O)cc(C(F)(F)F)n(C)c2=O)c(F)cc1Cl
methyl [3-{2-chloro-4-fluoro-5-[3-methyl-2,6-dioxo-4-(trifluoromethyl)-1,2,3,6-tetrahydropyrimidin-1-yl]phenoxy}-2-pyridyloxy]acetate
O=C([O-])[O-].[Na+].[Na+]
sodium carbonate
OC1CCCC1
cyclopentanol
Cn1c(C(F)(F)F)cc(=O)n(-c2cc(Oc3cccnc3OCC(=O)OC3CCCC3)c(Cl)cc2F)c1=O
cyclopentyl [3-{2-chloro-4-fluoro-5-[3-methyl-2,6-dioxo-4-(trifluoromethyl)-1,2,3,6-tetrahydropyrimidin-1-yl]phenoxy}-2-pyridyloxy]acetate

المذيبات

ظروف التفاعل

درجة الحرارة
100°CELSIUS
الظروف التفصيلية
See reaction.notes.procedure_details.

المعالجة

  1. 1
    workup.WAITat 120° C. for 2 hours
  2. 2
    درجة الحرارةThe reaction mixture was cooled to room temperature
  3. 3
    استخلاصthe mixture was extracted with ethyl acetate
  4. 4
    غسيلThe organic layer was washed with saturated aqueous sodium chloride solution
  5. 5
    تجفيفdried over anhydrous magnesium sulfate
  6. 6
    تركيزconcentrated

الإجراء التجريبي

A mixture of 0.30 g of methyl [3-{2-chloro-4-fluoro-5-[3-methyl-2,6-dioxo-4-(trifluoromethyl)-1,2,3,6-tetrahydropyrimidin-1-yl]phenoxy}-2-pyridyloxy]acetate (compound a-6), 0.06 g of sodium carbonate, and 3.0 ml of cyclopentanol was stirred at 100° C. for 1.5 hours and then at 120° C. for 2 hours. The reaction mixture was cooled to room temperature and then poured into water, and the mixture was extracted with ethyl acetate. The organic layer was washed with saturated aqueous sodium chloride solution, dried over anhydrous magnesium sulfate, and then concentrated. The residue was subjected to silica gel column chromatography to give 0.15 g of cyclopentyl [3-{2-chloro-4-fluoro-5-[3-methyl-2,6-dioxo-4-(trifluoromethyl)-1,2,3,6-tetrahydropyrimidin-1-yl]phenoxy}-2-pyridyloxy]acetate (compound a-28).

المصدر

DOI: 10.6084/m9.figshare.5104873.v1براءة الاختراع: US07115544B2uspto-grants-2006_10