Trifluoroacetic acid → 2,6-dichloro-9-methyl-8-(trifluoromethyl)-9H-purine

A mixture of 2,6-dichloro-N4-methylpyrimidine-4,5-diamine (400 mg) and trifluoroacetic acid (8 mL) was stirred for 8 hours while heating to reflux. Furthermore, the reaction mixture was stirred at 120° C. for 1.5 hours under microwave irradiation. After the reaction mixture was concentrated under reduced pressure, phenylphosphonic dichloride (1.8 mL) was added to the residue, and the mixture was stirred 180° C. for 2 hours. After the reaction mixture was cooled to room temperature, cold water (20 mL) was added thereto, then, the mixture was stirred, and the precipitate was collected by filtration. The obtained solid was purified by silica gel column chromatography (Hex:EtOAc=100:0 to 90:10), whereby 2,6-dichloro-9-methyl-8-(trifluoromethyl)-9H-purine (435 mg) was obtained as a white solid.

1. temperaturewhile heating to reflux
2. stirringFurthermore, the reaction mixture was stirred at 120° C. for 1.5 hours under microwave irradiation
3. concentrationAfter the reaction mixture was concentrated under reduced pressure, phenylphosphonic dichloride (1.8 mL)
4. additionwas added to the residue
5. stirringthe mixture was stirred 180° C. for 2 hours
6. additioncold water (20 mL) was added
7. stirringthe mixture was stirred
8. filtrationthe precipitate was collected by filtration
9. customThe obtained solid was purified by silica gel column chromatography (Hex:EtOAc=100:0 to 90:10)

ORD record

ord-9b1d7be61b274a77b6194c9bdda5f019

Source dataset

uspto-grants-2016_05

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09328118B2