Reaction #47935

Reaction equation

N-(4-(Trifluoromethyl)phenyl)-5,6,7,8-tetrahydropyrido[4,3-d]pyrimidin-4-amine

2,3-dichloropyridine

N,N-diisopropylethylamine

→

desired compound

Yield 26.0%

6-(3-Chloropyridin-2-yl)-N-(4-(trifluoromethyl)phenyl)-5,6,7,8-tetrahydropyrido[4,3-d]pyrimidin-4-amine

Yield 26.0%

Solvents

dioxane N,N-dimethylacetamide

Conditions

Workup

1. 1
   OtherThe solvents were removed under vacuum
2. 2
   workup.DISSOLUTIONthe residue was dissolved in ethyl acetate
3. 3
   Washwashed with sat. NaHCO3 and brine
4. 4
   DryingThe organic layer was dried over Na2SO4
5. 5
   Filtrationfiltered
6. 6
   Otherevaporated
7. 7
   Otherto give a brown residue
8. 8
   OtherThe residue was purified

Procedure

N-(4-(Trifluoromethyl)phenyl)-5,6,7,8-tetrahydropyrido[4,3-d]pyrimidin-4-amine (700 mg, 3.4 mmol) was dissolved in a mixture of dioxane/N,N-dimethylacetamide (4:1) (2 mL). To the mixture was added 2,3-dichloropyridine (1.5 g, 10.2 mmol) and N,N-diisopropylethylamine (0.87 mL, 5.1 mmol). The mixture was heated in a sealed tube at 150° C. in a microwave (Emrys Optimizer model, Personal Chemistry) for 16 h. The solvents were removed under vacuum and the residue was dissolved in ethyl acetate and washed with sat. NaHCO3 and brine. The organic layer was dried over Na2SO4, filtered and evaporated to give a brown residue. The residue was purified using a gradient of ethyl acetate:hexane (0-100%) to give the desired compound as an off-white powder (340 mg, 26%).

Source