| 93% |
With triethylamine In tetrahydrofuran at 25℃; for 6 h; |
A solution of2,4-Dichloro-7H-pyrrolo [2,3-d] pyrimidine (5.0 g, 26.6 mmol) was dissolved in tetrahydrofuran (50 mL)Triethylamine (4.0 g, 39.5 mmol) was added,Methyl iodide (4.2 g, 29.6 mmol) was added dropwise,After the addition was complete, the temperature was raised to 25 ° C and reacted for 16 hours.After the reaction was completed, the reaction solution was poured into water (100 mL)The precipitated solid was filtered,drying,The product (5.0 g, 93percent yield) was obtained. |
| 93% |
Stage #1: With sodium hydroxide In tetrahydrofuran at 0℃; for 0.25 h;
Stage #2: at 20℃; |
A 0 °C solution of 2,4-dichloro-7H-pyrrolo[2,3-d]pyrimidine (1.00 g, 5.32 mmol) in THF (8 mL) was stirred for 5 mm, then to the solution was added sodium hydroxide (255 mg, 6.38 mmol). The mixture was stirred for further 15 mm, and iodomethane (8.50 g, 53.20 mmol) was added. The mixture was stirred at rt overnight. To the reaction mixture was added H20 (100 mL), and the mixture was extracted with EtOAc (50 mL x 3). The combined organic layers were washed with saturated brine (80 mL), dried over anhydrous sodium sulfate, and filtered. The filtrate was concentrated in vacuo dry,and the residue was purified by silica gel column chromatography (PE/EtOAc (v/v) = 10/1) to give the title compound as a white solid (1.00 g, 93 percent).MS (ESI, pos. ion) m/z: 202.95 [M+Hfb. |
| 93% |
Stage #1: With sodium hydride In tetrahydrofuran at 0℃; for 0.25 h;
Stage #2: at 20℃; |
2,4-Dichloro-7H-pyrrolo[2,3-d]pyrimidine (1.00 g, 5.32 mmol)Dissolved in THF (8 mL), and the resulting solution was stirred at 0 ° C for 5 min.Then sodium hydride (255 mg, 6.38 mmol) was added thereto.The resulting reaction solution was stirred for 15 minutes.Methyl iodide (8.50 g, 53.20 mmol) was added thereto.The resulting reaction solution was transferred to room temperature and stirred overnight.The reaction was quenched by H2O (EtOAc) (EtOAc)The combined organic phases were washed with brine (80 mL).Dry over anhydrous sodium sulfate, filter, and concentrate the filtrate under reduced pressure.The residue was chromatographed on silica gel ( petroleum ether / ethyl acetate (v/v) = 10/1)Purification to give the title compound as a white solid(1.00g, 93percent). |
| 93% |
Stage #1: With sodium hydride In tetrahydrofuran at 0℃; for 0.25 h;
Stage #2: at 20℃; |
A solution of 2,4-dichloro-7H-pyrrolo[2,3-d]pyrimidine (1.00 g, 5.32 mmol) in THF (8 mL) was stirred at 0 °C for 5 mm. Then sodium hydride (255 mg, 6.38 mmol) was added. The resulting mixture was stirred for 15 mm, then iodomethane (8.50 g, 53.20 mmol) was added. The reaction mixture was warmed to rt and stirred overnight. H20 (100 mL) was added to quench the reaction, and the resulting mixture was extracted with EtOAc (50 mL x 3). The combined organic phases were washed with brine (80 mL), dried over anhydrous Na2504, filtered, and the filtrate was concentrated in vacuo. The residue was purified by silica gel chromatograph (PE/EtOAc (v/v) = 10/1) to give the tilte compound as a white solid (1.00 g, 93 percent).MS (ESI, pos. ion) m/z: 203.0 [M+H]t |
| 93% |
Stage #1: With sodium hydride In tetrahydrofuran at 0℃; for 0.25 h;
Stage #2: at 0 - 20℃; |
A solution of 2, 4-dichloro-7H-pyrrolo [2, 3-d] pyrimidine (1.00 g, 5.32 mmol) in THF (8 mL) was stirred for 5 min at 0 , then sodium hydride (255 mg, 6.38 mmol) was added. The mixture was stirred for 15 min, and then iodomethane (8.50 g, 53.20 mmol) was added. The resulting mixture was warm to rt and stirred overnight, then the reaction was quenched with H2O (100 mL) . The mixture was extracted with ethyl acetate (50 mL × 3) . The combined organic layers were washed with saturated brine (80 mL) , dried over anhydrous sodium sulfate and filtered. The filtrate was concentrated in vacuo, and the residue was purified by silica gel column chromatography (PE/EtOAc (v/v) =10/1) to give the title compound as a white solid (1.00 g, 93percent) .MS (ESI, pos. ion) m/z: 203.0 [M+H]+. |
| 84.1% |
Stage #1: With sodium hydride In tetrahydrofuran at 0℃; for 0.5 h;
Stage #2: at 0 - 20℃; |
To a solution of 60percent NaH (750 mg) in dry THF (20 mL), a solution of 18a (1.7 g) in dry THF (50 mL) was slowly added. The resulting solution was stirred at 0 °C for 30 min followed by the addition of MeI (0.79 mL) at 0 °C. The mixture was stirred at room temperature overnight. After the addition of 20 mL water, the solution was extracted with ether (3.x.10 mL) and washed with saturated brine. The organic phase was dried with anhydrous sodium sulfate and filtered. Ether was evaporated in vacuo to yield a crude residue, which was purified by silica gel chromatography (PE/EA= 10/1) to give 18d (1.53 g, yield: 84.1percent). ESI-MS calculated for (C7H5Cl2N3) [M+H]+, 202.0, found 202.1. |
| 74.1% |
Stage #1: With sodium hydride In tetrahydrofuran; mineral oil at 0℃;
Stage #2: at 20℃; |
A solution of 2,4-dichloro-7H-pyrrolo[2,3-d]pyrimidine (3.00 g, 16.0 mmol) in anhydrous tetrahydrofuran (45 mL) was cooled to 0° C. and treated with a 60percent dispersion of sodium hydride in mineral oil (0.83 g, 20.8 mmol). The reaction was stirred at 0° C. for 20-30 min. The reaction was then treated with iodomethane (3.65 g, 1.6 mL, 25.7 mmol), and the reaction stirred at room temperature overnight. The reaction was diluted with a saturated aqueous ammonium chloride solution (50 mL) and water (50 mL) and was extracted with a 10percent methanol in methylene chloride solution (4×50 mL). The combined organic layers were dried over magnesium sulfate, filtered and rinsed with methylene chloride, and concentrated in vacuo onto Celite®. Flash chromatography (80 g silica gel column, 0-15percent ethyl acetate/hexanes) afforded 2,4-dichloro-7-methyl-7H-pyrrolo[2,3-d]pyrimidine as a light yellow solid (2.39 g, 74.1percent). 1H NMR (400 MHz, DMSO-d6) δ ppm 3.81 (s, 3H) 6.70 (d, J=3.51 Hz, 1H) 7.76 (d, J=3.51 Hz, 1H). LC-MS calcd. for C7H6Cl2N3 [(M+H)+] 202, obsd. 202.0. |
| 58% |
Stage #1: With sodium hydride In acetonitrile at 0 - 20℃; for 0.333333 h;
Stage #2: at 20℃; for 1 h; |
To a solution of 2,4-dichloro-7H-pyrrolo[2,3-djpyrimidine 34 (237 mg, 1.26 mmol) in CH3CN (1 mL) was added NaH (33.3 mg, 1.39 mmol) portion- wise at 0 °C. The reaction mixture was stirred at room temperature for 20 mm until gas evolution was ceased. Methyl iodide (86.4 i.il, 1.39 mmol) was added and stirred the reaction mixture for 1 h at room temperature. To the reaction mixture was added water and extracted with ethyl acetate (2 x 30 mL). The combined organic layers were dried over Mg504, and then concentrated under vacuum. The resultant crude residue was purified by silica-gel column chromatography to afford 35 (144 mg, 58percent) as white solid. ‘H-NMR (400 MHz, DMSO-d6) ö 7.76 (d, J = 3.6 Hz, 1H), 6.71 (d, J = 3.6 Hz, 1H), 3.81 (s, 3H); MS: (m/z) [M+Hjb 204.02. |
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