Reaction #166292

Reaction equation

Ethyl acetate

5-Bromo-2,4-dichloropyrimidine

tetrahydro-2H-pyran-4-amine

N-ethyl-N-isopropylpropan-2-amine

→

(5-bromo-2-chloro-pyrimidin-4-yl)-(tetrahydro-pyran-4-yl)-amine

Yield 105.4%

Solvents

dioxane

Conditions

Workup

1. 1
   Washthe organic layer was washed with water and brine
2. 2
   DryingThe organic layer was dried with sodium sulfate
3. 3
   OtherRemoval of solvent

Procedure

5-Bromo-2,4-dichloropyrimidine (5.0 g, 21.9 mmol), tetrahydro-2H-pyran-4-amine (2.22 g, 21.9 mmol), and N-ethyl-N-isopropylpropan-2-amine (4.25 g, 32.9 mmol) were dissolved in dioxane (50 ml) and the reaction was stirred at room temperature for 12 hours. Ethyl acetate was added to the reaction mixture and the organic layer was washed with water and brine. The organic layer was dried with sodium sulfate. Removal of solvent gave (5-bromo-2-chloro-pyrimidin-4-yl)-(tetrahydro-pyran-4-yl)-amine (32) as a light yellow solid (6.75 g, 99%). 1H NMR (500 MHz, CD3OD) δ ppm 8.04 (1 H, s), 4.14-4.21 (1 H, m), 3.89 (2 H, dd, J=11.4, 4.3 Hz) 3.43 (2 H, td, J=11.9, 2.0 Hz), 1.80 (2 H, ddd, J=12.6, 4.2, 1.8 Hz), 1.63 (2 H, qd, J=12.2, 4.5, Hz); LCMS-ESI (POS), M/Z, M+1: Found 292.0, Calculated 292.

Source