تفاعل #1530676

معادلة التفاعل

DIAD

alcohol

1-{[2-(Hex-5-enyl-methyl-carbamoyl)-4-hydroxy-cyclopentanecarbonyl]-amino}-2-vinyl-cyclopropanecarboxylic acid ethyl ester

4-hydroxy-2-(3-isopropylpyrazol-1-yl)-7-methoxy-8-methylquinazoline

4-Hydroxy-2-(3-isopropylpyrazol-1-yl)-7-methoxy-8-methylquinazoline

triphenyl-phosphine

→

title compound

المردود 37.2%

1-({2-(Hex-5-enyl-methyl-carbamoyl)-4-[2-(3-isopropyl-pyrazol-1-yl)-7-methoxy-8-methyl-quinazolin-4-yloxy]-cyclopentanecarbonyl}-amino)-2-vinyl-cyclopropane-carboxylic acid ethyl ester

المردود 37.2%

المذيبات

DMF

ظروف التفاعل

المعالجة

1. 1
   workup.WAITAfter 12 h
2. 2
   أخرىthe reaction mixture was partitioned between ice-cold water and ether, organic layer
3. 3
   تجفيفwas dried (Na2SO4)
4. 4
   أخرىevaporated
5. 5
   أخرىThe residue was purified by column chromatography (gradient AcOEt/CH2Cl2, 1:9 to 10:0)

الإجراء التجريبي

DIAD (280 μL, 1.42 mmol) was added at −20° C. under nitrogen atmosphere to a solution of the alcohol (143) (367 mg, 0.90 mmol), 4-hydroxy-2-(3-isopropylpyrazol-1-yl)-7-methoxy-8-methylquinazoline (141) (270 mg, 0.90 mmol) and triphenyl-phosphine (288 mg, 1.42 mmol) in dry DMF (35 mL). After 2 h, the solution was warmed up to room temperature. After 12 h, the reaction mixture was partitioned between ice-cold water and ether, organic layer was dried (Na2SO4) and evaporated. The residue was purified by column chromatography (gradient AcOEt/CH2Cl2, 1:9 to 10:0) to give the title compound (230 mg, 34%), m/z=687 (M+H)+.

المصدر