Dichloromethane → 5-{8-[4-Acetyl-cis-3,5-dimethylpiperazin-1-yl]-9-(cyclopropylmethyl)-6-morpholin-4-yl-9H-purin-2-yl}pyrimidin-2-amine

Triethylamine (73.7 μl, 0.53 mmol) was added to a methylene chloride (10 ml)-dimethylformamide (1.5 ml) mixture solution of 5-{9-(cyclopropylmethyl)-8-[cis-3,5-dimethylpiperazin-1-yl]-6-morpholin-4-yl-9H-purin-2-yl}pyrimidin-2-amine (102.3 mg, 0.22 mmol) at room temperature followed by the addition of acetic anhydride (24.9 μl, 0.26 mmol) with ice cooling. The resulting mixture was stirred at room temperature for 3 days followed by the addition of acetic anhydride (6.2 μl, 0.07 mmol) and the resulting mixture was further stirred for 3 days. The reaction mixture was poured into methylene chloride-methanol (10:1) and the resulting mixture was washed with saturated aqueous sodium hydrogen carbonate solution and dried over anhydrous sodium sulfate. After filtration, the filtrate was concentrated under reduced pressure and the resulting residue was purified by preparative thin layer silica gel chromatography (methylene chloride:methanol=10:1) to 0.10 give the title compound (107.7 mg, 97%) as a pale yellow solid.

1. stirringthe resulting mixture was further stirred for 3 days
2. washthe resulting mixture was washed with saturated aqueous sodium hydrogen carbonate solution
3. dry with materialdried over anhydrous sodium sulfate
4. filtrationAfter filtration
5. concentrationthe filtrate was concentrated under reduced pressure
6. customthe resulting residue was purified by preparative thin layer silica gel chromatography (methylene chloride:methanol=10:1) to 0.10

ORD record

ord-1fde658bfde04a8b9291288c051f6398

Source dataset

uspto-grants-2012_11

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08309546B2