Réaction #70282

Équation de réaction

methyl 2-amino-5-cyclopropylbenzoate

Cs2CO3

5-bromo-2-chloropyrimidine

Xantphos

→

expected product

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

Solvants

dioxane

ethyl acetate

Water

Conditions de réaction

Traitement

1. 1
   ExtractionThe aqueous phase was extracted again with more ethyl acetate
2. 2
   LavageThe organic phase was washed with water and brine
3. 3
   Autredried
4. 4
   Filtrationfiltered
5. 5
   Concentrationconcentrated in vacuo
6. 6
   AutreThe crude mixture was purified by reverse chromatography (Water: MeOH/AcN 1:1 from 0% to 100%)
7. 7
   Autreaffording

Mode opératoire

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.

Source