Propylenediamine → HCID 86633869, compound

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).

1. customA precipitate formed
2. additionwere added simultaneously via two syringes
3. temperatureexternal cooling
4. customwas removed
5. customThe reaction was then partitioned between CH2Cl2 (100 mL) and sat. NaHCO3 (100 mL)
6. customThe layers were separated
7. extractionthe aqueous layer was extracted with CH2Cl2 (50 mL)
8. dry with materialThe combined organic layers were dried (sodium sulfate)
9. filtrationfiltered
10. concentrationconcentrated under reduced pressure onto silica gel
11. customPurification
12. customby silica gel chromatography (dry loaded)

ORD record

ord-56988c0586924597a564a5efdd0f7b46

Source dataset

uspto-grants-2012_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08148391B2