تفاعل #324396

معادلة التفاعل

3,5-bis[4-(tert-butyldimethylsilyloxy)phenyl]pyrazin-2-amine

2-[4-(tert-butyldimethylsilyloxy)phenyl]acetyl chloride

water

→

Compound 11j

المردود 81.1%

N-[3,5-Bis{4-(tert-butyldimethylsilyloxy)phenyl}pyrazin-2-yl]-2-[4-(tert-butyldimethylsilyloxy)phenyl]acetamide

المردود 81.1%

المذيبات

pyridine

ظروف التفاعل

المعالجة

1. 1
   أخرىprepared above at 0° C.
2. 2
   درجة الحرارةthe mixture was heated
3. 3
   درجة الحرارةAfter cooling to room temperature
4. 4
   استخلاصthe product was extracted with ethyl acetate (200 mL×3)
5. 5
   استخلاصThe combined organic extract
6. 6
   غسيلwas washed successively with water (200 mL) and brine (200 mL)
7. 7
   تجفيفby drying over anhydrous sodium sulfate
8. 8
   ترشيحAfter filtration and concentration under reduced pressure
9. 9
   أخرىthe residue was purified by column chromatography (silica gel 50 g, n-hexane/ethyl acetate=4/1)

الإجراء التجريبي

Under an argon atmosphere, to a mixture of 3,5-bis[4-(tert-butyldimethylsilyloxy)phenyl]pyrazin-2-amine (7j) (591 mg, 1.16 mmol) and 4-(dimethylamino)pyridine (15.7 mg, 129 μmol) dissolved in anhydrous pyridine (20 mL) was added 2-[4-(tert-butyldimethylsilyloxy)phenyl]acetyl chloride (10) prepared above at 0° C. and the mixture was heated with stirring at 50° C. for 15 hours. After cooling to room temperature, to this was added water and the product was extracted with ethyl acetate (200 mL×3). The combined organic extract was washed successively with water (200 mL) and brine (200 mL), followed by drying over anhydrous sodium sulfate. After filtration and concentration under reduced pressure, the residue was purified by column chromatography (silica gel 50 g, n-hexane/ethyl acetate=4/1) to give Compound 11j (714 mg, 945 μmol, 81.1%) as a yellow foamy solid. Rf=0.37 (n-hexane/diethyl ether=2/3); 1H NMR (400 MHz, DMSO-d6) δ 0.14 (s, 6H), 0.19 (s, 6H), 0.20 (s, 6H), 0.92 (s, 9H), 0.95 (s, 18H), 3.47 (s, 2H), 6.71-6.78 (2AA′BB′, 4H), 6.94-7.02 (AA′BB′, 2H), 7.03-7.13 (AA′BB′, 2H), 7.57-7.63 (AA′BB′, 2H), 8.03-8.10 (AA′BB′, 2H), 8.91 (s, 1H), 10.49 (s, 1H); 13C NMR (75.5 MHz, DMSO-d6) δ −4.5 (6C), 17.9 (3C), 25.5 (9C), 41.7, 119.3 (2C), 119.5 (2C), 120.3 (2C), 127.9, 128.1 (2C), 128.9, 129.3 (2C), 130.4 (2C), 130.7, 136.9, 142.4, 147.2, 147.8, 153.8, 155.7, 156.7, 169.3; IR (KBr, cm−1) 523, 637, 677, 710, 781, 804, 839, 914, 1009, 1078, 1105, 1169, 1258, 1362, 1402, 1416, 1441, 1472, 1510, 1605, 1667, 2857, 2886, 2928, 2955, 3036, 3221; HRMS (ESI+) m/z 778.3853 ([M+Na]+, C42H61N3NaO4Si3+ requires 778.3862).

المصدر