تفاعل #1358400

معادلة التفاعل

7-bromo-2-methyl-4-pyrrolidin-1-yl-quinazoline

caesium carbonate

trans-1,2-diaminocyclohexane

2-furamide

→

furan-2-carboxylic acid (2-methyl-4-pyrrolidin-1-yl-quinazolin-7-yl)-amide

المردود 22.0%

المذيبات

dioxane

ظروف التفاعل

المعالجة

1. 1
   درجة الحرارةheated
2. 2
   درجة الحرارةat reflux under argon for 20 h
3. 3
   أخرىThe reaction mixture was partitioned between EtOAc and water
4. 4
   أخرىthe layers were separated
5. 5
   غسيلthe organic layer washed twice with water
6. 6
   تجفيفdried over sodium sulphate
7. 7
   تركيزconcentrated in vacuo
8. 8
   تركيزCombination of the purified fractions and concentration in vacuo

الإجراء التجريبي

A suspension of 0.12 g (0.41 mmol) of 7-bromo-2-methyl-4-pyrrolidin-1-yl-quinazoline, 3.9 mg (0.021 mmol) of copper (I) iodide and 0.267 g (0.82 mmol) of caesium carbonate in dioxane (5 ml) was treated at RT under argon with 4.7 mg (0.041 mmol) of trans-1,2-diaminocyclohexane and 0.18 g (1.6 mmol) of 2-furamide and then heated at reflux under argon for 20 h. The reaction mixture was partitioned between EtOAc and water, the layers were separated, the organic layer washed twice with water dried over sodium sulphate and concentrated in vacuo. The residue was applied to silica gel column with CH2Cl2/MeOH/NH4OH (9:1:0.5) as eluent. Combination of the purified fractions and concentration in vacuo gave 29 mg (22%) of the furan-2-carboxylic acid (2-methyl-4-pyrrolidin-1-yl-quinazolin-7-yl)-amide as an off white solid. ISP mass spectrum, m/e: 323.4 (M+1 calculated for C18H18N4O2: 323).

المصدر