Réaction #69648

Équation de réaction

HCl diethylether

4-[[5-bromo-4-(4-cyano-2,6-dimethylphenoxy)-6-chloro-2-pyrimidinyl]amino]benzonitrile

tetrahydrofuran

1-pyrrolidineethanamine

→

4-[[5-bromo-4-(4-cyano-2,6-dimethylphenoxy)-6-[(1-pyrrolidinyl)ethylamino]-2-pyrimidinyl]amino]benzonitrile hydrochloride

Rendement 50.6%

Solvants

CH2Cl2

CH3CN

Conditions de réaction

Traitement

1. 1
   Lavagethe mixture was washed with water
2. 2
   Autredried
3. 3
   Filtrationfiltered
4. 4
   Autrethe filtrate was evaporated
5. 5
   AutrePurification
6. 6
   Lavageeluting with 1:9 methanol
7. 7
   Autremethylene chloride produced a solid which
8. 8
   Températurethe mixture was cooled in ice
9. 9
   FiltrationFiltration

Mode opératoire

4-[[5-bromo-4-(4-cyano-2,6-dimethylphenoxy)-6-chloro-2-pyrimidinyl]amino]benzonitrile (0.000660 mol), tetrahydrofuran (1 ml), and 1-pyrrolidineethanamine (0.00198 mol) were added to a pressure vessel. The mixture was heated at 75° C. for 16 hours. CH2Cl2 was added, and the mixture was washed with water, dried, filtered and the filtrate was evaporated. Purification using flash column chromatography eluting with 1:9 methanol:methylene chloride produced a solid which was redissolved in CH3CN. HCl/diethylether 1.0M (0.48 ml) was added, and the mixture was cooled in ice. Filtration yielded 0.19 g of 4-[[5-bromo-4-(4-cyano-2,6-dimethylphenoxy)-6-[(1-pyrrolidinyl)ethylamino]-2-pyrimidinyl]amino]benzonitrile hydrochloride (1:1) (50.6%); mp. 208-210° C. (comp. 47).

Source