Reaktion #58357

Reaktionsgleichung

4-chloro-2-methylsulfanyl-6-phenylamino-pyrimidine-5-carbaldehyde

K2CO3

phenylboronic acid

→

2-methylsulfanyl-4-phenyl-6-phenylamino-pyrimidine-5-carbaldehyde

Ausbeute 70.0%

Lösungsmittel

dioxane

H2O

Reaktionsbedingungen

Aufarbeitung

1. 1
   SonstigeThe reaction mixture was degassed
2. 2
   TemperaturThe reaction mixture was then heated
3. 3
   Temperaturunder reflux for 24 h
4. 4
   Temperaturcooled 23°
5. 5
   Sonstigethe layers were separated
6. 6
   workup.ADDITIONwas added
7. 7
   Sonstigethe organic layer was separated
8. 8
   Waschenwashed with sat'd aqueous (hereinafter “aq”) NaCl
9. 9
   Trocknendried (MgSO4)
10. 10
    Filtrationfiltered
11. 11
    SonstigeThe yellow solution was then evaporated
12. 12
    SonstigeProduct was purified by column chromatography or by crystallization from 10 mL of isopropanol: H2O (2:1)

Vorschrift

To a solution of 4-chloro-2-methylsulfanyl-6-phenylamino-pyrimidine-5-carbaldehyde (300 mg, 1.07 mmol) in dioxane (21 mL) and H2O (7 mL) was added anhydrous K2CO3 (443 mg, 3.21 mmol, 3 eq) followed by phenylboronic acid (196 mg, 1.6 mmol, 1.5 eq). The reaction mixture was degassed and tetrakis(triphenylphosphine)-palladium (61 mg, 0.053 mmol, 0.05 eq) was added. The reaction mixture was then heated under reflux for 24 h and cooled 23°, the layers were separated, EtOAc (50 mL), followed by H2O (10 mL), was added, the organic layer was separated, washed with sat'd aqueous (hereinafter “aq”) NaCl, dried (MgSO4) and filtered. The yellow solution was then evaporated. Product was purified by column chromatography or by crystallization from 10 mL of isopropanol: H2O (2:1) to give 240 mg (70% yield) of pure 2-methylsulfanyl-4-phenyl-6-phenylamino-pyrimidine-5-carbaldehyde. 1H-NMR δ 2.60 (s, 3H), 7.22 (m, 1H), 7.35-7.81 (m, 9H), 9.89 (s, 1H), 11.31 (br s, 1H), LC MS (m/e)=322 (MH+).

Quelle