Реакция #58357

Уравнение реакции

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

K2CO3

phenylboronic acid

→

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

Выход 70.0%

Растворители

dioxane

H2O

Условия реакции

Обработка

1. 1
   ДругоеThe reaction mixture was degassed
2. 2
   ТемператураThe reaction mixture was then heated
3. 3
   Температураunder reflux for 24 h
4. 4
   Температураcooled 23°
5. 5
   Другоеthe layers were separated
6. 6
   workup.ADDITIONwas added
7. 7
   Другоеthe organic layer was separated
8. 8
   Промывкаwashed with sat'd aqueous (hereinafter “aq”) NaCl
9. 9
   Сушкаdried (MgSO4)
10. 10
    Фильтрацияfiltered
11. 11
    ДругоеThe yellow solution was then evaporated
12. 12
    ДругоеProduct was purified by column chromatography or by crystallization from 10 mL of isopropanol: H2O (2:1)

Методика

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+).

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