Cesium carbonate → 5-Methyl-6-[4-(morpholin-4-yl)cyclohex-1-en-1-yl]pyridin-3-amine

Temperature

100 °C

Acetylacetone (0.31 ml) and 28% ammonia water (1.78 ml) were added to a suspension of 4-[4-(5-bromo-3-methylpyridin-2-yl)cyclohex-3-en-1-yl]morpholine (2 g), copper acetylacetonate (466 mg) and cesium carbonate (3.86 g) in N,N-dimethylformamide (12 ml), sealed in a tube under nitrogen atmosphere and stirred at 100° C. for 20 hours. After completion of the reaction, the reaction solution was left stand to room temperature and concentrated. The resulting residue was diluted with water and extracted with chloroform. The organic layer was dried over anhydrous sodium sulfate and concentrated. The resulting residue was purified with silica gel column chromatography (chlorofolin/methanol) to give the titled compound (1.31 g) as a pale yellow solid.

1. customsealed in a tube under nitrogen atmosphere
2. customAfter completion of the reaction
3. waitthe reaction solution was left stand to room temperature
4. concentrationconcentrated
5. additionThe resulting residue was diluted with water
6. extractionextracted with chloroform
7. dry with materialThe organic layer was dried over anhydrous sodium sulfate
8. concentrationconcentrated
9. customThe resulting residue was purified with silica gel column chromatography (chlorofolin/methanol)

ORD record

ord-849469cc25c44838980b3b80b07f071e

Source dataset

uspto-grants-2015_10

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09150555B2