Propylenediamine → HCID 86633869, compound

Participants

Reaction Steps

1,2-Diaminopropane (2.00 g, 27.03 mmol, 2.30 mL, 1.5 eq.) in THF (100 mL) was cooled to 0° C. and 2,4,5-trichloropyrimidine (3.30 g, 18.02 mmol, 2.06 mL, 1.0 eq.) was added. A precipitate formed and the reaction was stirred for 5 minutes before NEt3 and mesyl chloride were added simultaneously via two syringes. After 5 minutes, external cooling was removed and the reaction was stirred under a nitrogen atmosphere for 45 minutes. The reaction was then partitioned between CH2Cl2 (100 mL) and sat. NaHCO3 (100 mL). The layers were separated and the aqueous layer was extracted with CH2Cl2 (50 mL). The combined organic layers were dried (sodium sulfate), filtered, and concentrated under reduced pressure onto silica gel. Purification by silica gel chromatography (dry loaded) using a gradient of 0-10% MeOH/CH2Cl2 as the eluting solvent to obtain N-[2-(2,5-dichloro-pyrimidin-4-ylamino)-1-methyl-ethyl]-methanesulfonamide as a white solid (1.75 g, 32%). m.p.=160° C.; LCMS (m/e) 299 (M+1); 1H-NMR (d6-DMSO, 400 MHz) δ 8.20 (s, 1H), 7.94-7.77 (m, 1H), 7.23-7.07 (m, 1H), 3.65 (m, 1H), 3.42-3.35 (m, 2H), 2.93 (s, 3H), 1.11 (d, 3H, J=6.5 Hz).

Provenance & Evidence