Reaktion #70282

Reaktionsgleichung

methyl 2-amino-5-cyclopropylbenzoate

Cs2CO3

5-bromo-2-chloropyrimidine

Xantphos

→

expected product

Methyl 2-(2-chloropyrimidin-5-ylamino)-5-cyclopropylbenzoate

Lösungsmittel

dioxane

ethyl acetate

Water

Reaktionsbedingungen

Aufarbeitung

1. 1
   ExtraktionThe aqueous phase was extracted again with more ethyl acetate
2. 2
   WaschenThe organic phase was washed with water and brine
3. 3
   Sonstigedried
4. 4
   Filtrationfiltered
5. 5
   Einengenconcentrated in vacuo
6. 6
   SonstigeThe crude mixture was purified by reverse chromatography (Water: MeOH/AcN 1:1 from 0% to 100%)
7. 7
   Sonstigeaffording

Vorschrift

In a schlenck tube, a mixture of methyl 2-amino-5-cyclopropylbenzoate (described in Intermediate 8 (step A) (26.15 mmol, 5 g), 5-bromo-2-chloropyrimidine (26.93 mmol, 5.21 g), Xantphos (1.07 mmol, 0.6 g), Pd2(dba)3 (1.07 mmol, 0.6 g) and Cs2CO3 (36.65 mmol, 11.9 g) in dioxane (210 ml) was heated at 100° C. overnight. Water and ethyl acetate were added to the reaction crude. The aqueous phase was extracted again with more ethyl acetate. The organic phase was washed with water and brine, dried, filtered and concentrated in vacuo. The crude mixture was purified by reverse chromatography (Water: MeOH/AcN 1:1 from 0% to 100%) affording 6 g (60% of yield) of the expected product.

Quelle