Reaktion #1358400

Reaktionsgleichung

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

Ausbeute 22.0%

Lösungsmittel

dioxane

Reaktionsbedingungen

Aufarbeitung

1. 1
   Temperaturheated
2. 2
   Temperaturat reflux under argon for 20 h
3. 3
   SonstigeThe reaction mixture was partitioned between EtOAc and water
4. 4
   Sonstigethe layers were separated
5. 5
   Waschenthe organic layer washed twice with water
6. 6
   Trocknendried over sodium sulphate
7. 7
   Einengenconcentrated in vacuo
8. 8
   EinengenCombination of the purified fractions and concentration in vacuo

Vorschrift

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).

Quelle