반응 #56872

반응 방정식

triphenylphosphine

sodium carbonate

2-methyl-5-bromo-phenylboronic acid

2-amino-4,6-dichloropyrimidine

→

2-amino-4-chloro-6-(2-methyl-5-bromo-phenyl)-pyrimidine

수율 80.1%

용매

water

water

반응 조건

후처리

1. 1
   기타degassed ethylene glycol dimethyl ether (150 ml)
2. 2
   workup.STIRRINGAfter stirring for 16 hours
3. 3
   추출extracted with ethyl acetate (3×100 ml)
4. 4
   세척The combined extracts were washed with water (100 ml)
5. 5
   건조dried over sodium sulfate
6. 6
   농축concentrated under reduced pressure
7. 7
   기타The residue was purified by flash chromatography on silica gel eluting with ethyl acetate-hexane (1:4)

실험 절차

To a mixture of 2-methyl-5-bromo-phenylboronic acid (7.0 g, 32.6 mmol), 2-amino-4,6-dichloropyrimidine (6.95 g, 42.4 mmol), and degassed ethylene glycol dimethyl ether (150 ml) was added a solution of sodium carbonate (17.3 g, 163 mmol) in water (50 ml). The mixture was stirred vigorously and palladium acetate (0.73 g, 3.26 mmol) was added followed by triphenylphosphine (1.71 g, 6.52 mmol). After stirring for 16 hours, the mixture was diluted with water (100 ml) and extracted with ethyl acetate (3×100 ml). The combined extracts were washed with water (100 ml), dried over sodium sulfate, and concentrated under reduced pressure. The residue was purified by flash chromatography on silica gel eluting with ethyl acetate-hexane (1:4) to provide 2-amino-4-chloro-6-(2-methyl-5-bromo-phenyl)-pyrimidine (7.8 g, 80% yield) as a pale yellow powder. 1H NMR (DMSO-d6) δ 7.58 (d, J=2.0 Hz, 1H), 7.55 (dd, J=2.0, 8.1 Hz, 1H), 7.28 (d, J=8.1 Hz, 1H), 7.26 (br s, 2H), 6.86 (s, 1H), 2.32 (s, 3H).

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