Trifluoroacetic acid → 7-chloro-5-(1H-pyrazol-4-yl)imidazo[1,2-c]pyrimidine

To a solution of 7-chloro-5-(1-((2-(trimethylsilyl)ethoxy)methyl)-1H-pyrazol-4-yl)imidazo[1,2-c]pyrimidine (Preparation G; 0.250 g, 0.715 mmol) in 3.5 mL of DCM was added 2,2,2,-trifluoroacetic acid (2.2 mL, 28.6 mmol) and allowed to stir at ambient temperature for 1 hour before the reaction mixture was diluted with 5 mL of toluene and then concentrated under reduced pressure. The resulting residue was dissolved in 2 mL of 7M ammonia in methanol and stirred at ambient temperature for 30 minutes. The reaction mixture was concentrated under reduced pressure and the resulting residue was purified by silica gel chromatography eluting with a gradient of 2-5% methanol in DCM with 1% ammonium hydroxide to afford 7-chloro-5-(1H-pyrazol-4-yl)imidazo[1,2-c]pyrimidine (0.107 g, 0.468 mmol, 65.5% yield). MS (apci) m/z=220.1 (M+H).

1. concentrationconcentrated under reduced pressure
2. dissolutionThe resulting residue was dissolved in 2 mL of 7M ammonia in methanol
3. stirringstirred at ambient temperature for 30 minutes
4. concentrationThe reaction mixture was concentrated under reduced pressure
5. customthe resulting residue was purified by silica gel chromatography
6. washeluting with a gradient of 2-5% methanol in DCM with 1% ammonium hydroxide

ORD-Eintrag

ord-d75c1c52ff91492baf82ac112123ec04

Quelldatensatz

uspto-grants-2015_02

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US08962596B2