تفاعل #2814

معادلة التفاعل

sodium hydride

IV

(E)-N-tert-Butyloxycarbonyl-4-(5-pyrimidinyl)-3-butene-1-amine

iodomethane

diisopropylamine

→

compound V

المردود 76.1%

(E)-N-Methyl-N-tert-Butyloxycarbonyl-4-(5-pyrimidinyl)-3-butene-1-amine

المردود 76.1%

المذيبات

water

1,2-dimethoxyethane

DMF

water

1,2-dimethoxyethane

ظروف التفاعل

المعالجة

1. 1
   workup.STIRRINGThe mixture was stirred at ambient temperature for 3 days
2. 2
   درجة الحرارةcooled
3. 3
   استخلاصextracted with chloroform (7×50 mL)
4. 4
   أخرىdried (Na2 SO4)
5. 5
   ترشيحfiltered
6. 6
   تركيزconcentrated by rotary evaporation
7. 7
   أخرىThe residue was dried under high vacuum at ambient temperature
8. 8
   أخرىto give a red-brown oil
9. 9
   أخرىThe oil was chromatographed on silica gel (50 g)
10. 10
    غسيلeluting with ethyl acetate
11. 11
    تركيزconcentrated by rotary evaporation
12. 12
    أخرىdried under high vacuum at ambient temperature

الإجراء التجريبي

Under a nitrogen atmosphere, sodium hydride (0.78 g, 19.5 mmol, 60% dispersion in oil) was added to a stirring solution of IV (0.50 g, 2.0 mmol), 1,2-dimethoxyethane (20 mL), DMF (25 mL), and a trace of diisopropylamine. The mixture was stirred at ambient temperature for 45 min, and a solution of iodomethane (2.59 g, 18.3 mmol) in 1,2-dimethoxyethane (5 mL) was added. The mixture was stirred at ambient temperature for 3 days, cooled, and water (25 mL) was added dropwise. The mixture was diluted with water (200 mL) and extracted with chloroform (7×50 mL). All chloroform extracts were combined, dried (Na2 SO4), filtered, and concentrated by rotary evaporation. The residue was dried under high vacuum at ambient temperature to give a red-brown oil, The oil was chromatographed on silica gel (50 g), eluting with ethyl acetate. Selected fractions were combined, concentrated by rotary evaporation, and dried under high vacuum at ambient temperature to give compound V as a light yellow oil (0.40 g, 76.1%).

المصدر