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Step-1: 2-Chloro-7-methyl-7H-pyrrolo[2,3-d]pyrimidine [0182] To a stirred solution of 2-chloro-7H-pyrrolo[2,3-d]pyrimidine (1 g, 6.5 mmol) in MeCN (25 mL) at 5 oC was added NaH (313 mg, 7.8 mmol). The resultant mixture was brought to room temperature and stirred for 30 min. Then MeI was added at 0 oC and continued stirring at room temperature for overnight. The reaction mixture was filtered through a pad of celite and washed with MeCN (10 mL). The filtrate was concentrated and recrystallized from Et2O. The mother liquor was concentrated and purified by ISCO (SiO2: DCM/EtOAc 0 to 30%). Altogether, the recrystallized and purified provided the pure compound (835 mg, 77%).
47%
With potassium carbonate; In N,N-dimethyl-formamide; at 20℃; for 3h;Sealed tube;
Step 1. 2-chloro-7-methyl-7H-pyrrolo[2,3-d]pyrimidineTo a solution of 2-chloro-7H-pyrrolo[2,3-d]pyrimidine (27 mg, 0.16 mmol, prepared as reported in Bioorganic and Medicinal Chemistry Letters, 16(22), 5778-5783 (2006)) in DMF (0.15 mL) was added potassium carbonate (67 mg, 0.48 mmol), followed by methyl iodide (10 microL, 0.16 mmol). The mixture was stirred in a sealed vial at RT for 3 h. The reaction was diluted with DCM and acetonitrile, filtered and concentrated. The product was purified by flash column chromatography on silica gel, eluting with 0-50% ethyl acetate in hexanes to afford product as a white solid (13 mg, 47%). LCMS (M+H)+: 167.9, 169.9.
47.4%
To a solution of NaH (106.6 mg, 2.67 mmol) in THF (5 mL) was added 2-chloro- 7H-pyrrolo[2,3-d]pyrimidine (500 mg, 2.54 mmol) at 0C and stirred for 30 minutes at the same temperature. CH3I (1.5 g, 10.2 mmol) was added at 0C and the combined mixture stirred for 3 h at 15C. After TLC showed the reaction was complete, the mixture was diluted with water 20 mL) and extracted with ethyl acetate EA (2x20 mL) and the combined organic layers were washed with brine (30 mL), dried over Na2S04 and concentrated to give the title compound (254 mg, 47.4%) as colorless oil which was used in next step without further purification.
1-(3-(2-chloro-7H-pyrrolo[2,3-d]pyrimidin-7-yl)phenyl)-N,N-dimethylmethylamine[ No CAS ]
Yield
Reaction Conditions
Operation in experiment
6%
With pyridine; copper diacetate; In methanol; at 25.0℃; for 80.0h;
Add 2-chloro-7H-pyrrolo [2,3-d] pyrimidine (200 mg, 1.33 mmol) and3-((dimethylamino) methyl) phenylboronic acid (561mg, 2.60mmol) was dissolved in methanol (10mL),Copper acetate (787.92 mg, 3.91 mmol) and pyridine (420.47 mg, 5.21 mmol) were added, and the reaction was left open at 25 C for 80 hours.The reaction solution was poured into water and extracted with ethyl acetate. The organic phases were combined,It was washed with saturated brine, dried over anhydrous sodium sulfate, and filtered.The filtrate was concentrated, and the residue was purified by preparative thin layer chromatography (eluent: petroleum ether / ethyl acetate = 1/2),The title compound (50 mg, yield: 6.0%) was obtained in this step.
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