Triethylamine → HCID 59333607, compound

1-Hydroxybenzotriazole monohydrate (35.1 mg, 0.23 mmol), 1-(dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (65.9 mg, 0.34 mmol), and triethylamine (86.2 μl, 0.62 mmol) were added to an N,N-dimethylformamide suspension (2.0 ml) of 5-[9-(cyclopropylmethyl)-6-morpholin-4-yl-8-piperazin-1-yl-9H-purin-2-yl]pyrimidin-2-amine (100.0 mg, 0.23 mmol) and N-tert-butoxycarbonyl-N-methylglycine (52.0 mg, 0.27 mmol) at room temperature. The resulting mixture was stirred for 3 days and the reaction mixture was poured into dichloromethane-methanol (10:1), washed with saturated aqueous sodium bicarbonate solution and dried over anhydrous sodium sulfate. After filtration, the filtrate was concentrated under reduced pressure and the resulting residue was dissolved in dichloromethane (4.0 ml) followed by the addition of trifluoroacetic acid (2.0 ml) with ice cooling. The resulting mixture was stirred at room temperature for 2 hours and concentrated, dichloromethane was added to the residue, and the resulting mixture was neutralized with saturated aqueous sodium hydrogen carbonate solution. The resulting mixture was extracted with dichloromethane-methanol (10:1), dried over anhydrous sodium sulfate, and filtrated, the filtrate was concentrated under reduced pressure, and the resulting residue was purified by preparative thin layer silica gel chromatography (dichloromethane:methanol=5:1) to give the title compound (67.1 mg, 58%) as a pale yellow solid.

1. washwashed with saturated aqueous sodium bicarbonate solution
2. dry with materialdried over anhydrous sodium sulfate
3. filtrationAfter filtration
4. concentrationthe filtrate was concentrated under reduced pressure
5. dissolutionthe resulting residue was dissolved in dichloromethane (4.0 ml)
6. additionfollowed by the addition of trifluoroacetic acid (2.0 ml) with ice cooling
7. stirringThe resulting mixture was stirred at room temperature for 2 hours
8. concentrationconcentrated
9. additiondichloromethane was added to the residue
10. extractionThe resulting mixture was extracted with dichloromethane-methanol (10:1)
11. dry with materialdried over anhydrous sodium sulfate
12. filtrationfiltrated
13. concentrationthe filtrate was concentrated under reduced pressure
14. customthe resulting residue was purified by preparative thin layer silica gel chromatography (dichloromethane:methanol=5:1)

ORD record

ord-dd2033dea224463592b67725149b37a9

Source dataset

uspto-grants-2012_11

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08309546B2