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With N-Bromosuccinimide; In dichloromethane; at 0 - 25℃; for 2.0h;
Example 1 5-(1H-1,3-Benzodiazol-2-yl)-7-methyl-N-phenyl-7H-pyrrolo[2,3-d]pyrimidin-4-amine[0122]STEP 1: 5-Bromo-4-chloro-7-methyl-7H-pyrrolo[2,3-d]pyrimidine [Chem. 3]To a stirred solution of 4-chloro-7-methyl-7H-pyrrolo[2,3-d]pyrimidine (WO2005/095357, 6.02 g, 35.9 mmol) in dichloromethane (120 mL) was added N-bromosuccinimide (7.67 g, 43.1 mmol) at 0 oC. The resulting mixture was stirred at room temperature for 2 hrs. The reaction mixture was quenched with saturated sodium bicarbonate aqueous solution (200 mL), and extracted with dichloromethane (200 mL). The organic layer was dried over magnesium sulfate, and concentrated under reduced pressure. The residue was purified by silica-gel column chromatography (dichloromethane/ethyl acetate=10/1) to give the title compound (8.27 g, 93%) as a white solid.;LCMS (Method A) m/z: M+1 247.9; tR = 2.70 min.
86%
With N-Bromosuccinimide; In dichloromethane; at 15 - 23℃; for 3.0h;
Add N-bromosuccinimide (418 g, 2.35 mol) portionwise over 20 min at 15 C to a solution of 4-chloro-7-methyl-pyrrolo[2,3-d]pyrimidine (355 g, 2.12 mol) indichloromethane (3.19 L), and stir at 23 C for 3 h. After this time, filter, wash with H20 (5.32 L), and dry to give the title compound (448 g, 86%) as a white solid. ES/MS m/z (35C1,79Br) 245.9 (M+H).
With N-Bromosuccinimide; In dichloromethane; at 20℃;
5-bromo-4-chloro-7-methyl-7H-Dyrrolo[2,3-dlDyrimidineTo 4-chloro-7-methyl-7H-pyrrolo[2,3-d]pyrimidine (12.15 g, 72.5 mmol) in Dichloromethane (DCM) (200 ml.) was added NBS (13.55 g, 76 mmol) portionwise, and the reaction mixture was stirred overnight at room temperature. The solvent was evaporated, and the solid was washed with water and dried to afford 5-bromo-4-chloro-7- methyl-7H-pyrrolo[2,3-d]pyrimidine (17 g) as an off-white solid.
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