1,2-Ethanediamine, N1,N1,N2-trimethyl- → HCID 86649360, compound

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Reaction Conditions

Reaction Steps

A mixture of 4-chloropyrimidin-2-amine (CAS#3993-78-0, 0.100 g, 0.00077 mole), N1,N1,N2-trimethylethane-1,2-diamine (CAS#142-25-6, 0.082 g, 0.00077 mole), and N-ethyl-N-isopropylpropan-2-amine (0.94 mL, 0.00540 mole) in n-propanol (2 mL) was heated at 200° C. under microwave irradiation for 15 minutes. Volatiles were removed under reduced pressure and the residue was partitioned between ethyl acetate and saturated aqueous sodium carbonate. The organic layer was dried (MgSO4) and filtered. The filtrate was concentrated under reduced pressure and the residue was purified by chromatography with silica gel, eluting with 97:3:0.5 to 95:5:1 DCM/MeOH/Et3N. Fractions containing product were combined and concentrated under reduced pressure. The residue was dissolved in ethyl acetate. This solution was dried (MgSO4) and filtered. The filtrate was concentrated under reduced pressure and the residue was dissolved in a minimum of methanol. This solution was acidified with a 4.0 M solution of HCl in dioxane. Ether was added to induce crystallization. Crystals were collected by filtration to provide N4-(2-(dimethylamino)ethyl)-N4-methylpyrimidine-2,4-diamine dihydrochloride (0.035 g, 15.8% yield). 1H NMR (300 MHz, CD3OD) δ ppm 3.00 (s, 6H), 3.25 (s, 3H), 3.46 (t, J=6 Hz, 2H), 4.14 (t, J=6 Hz, 2H), 6.40 (d, J=7 Hz, 1H), 7.75 (d, J=7 Hz, 1H). MS (DCl—NH3) m/z=196 (M+H)+.

Provenance & Evidence