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CAS No. : | 1266343-30-9 | MDL No. : | MFCD14635647 |
Formula : | C7H5BrClN3 | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | N/A |
M.W : | 246.49 | Pubchem ID : | 66545160 |
Synonyms : |
|
TPSA :Topological Polar Surface Area | 30.7 | H-Bond Acceptor Count : | 2 |
XLogP3 : | 2.3 | H-Bond Donor Count : | 0 |
SP3 : | 0.14 | Rotatable Bond Count : | 0 |
Signal Word: | Warning | Class: | N/A |
Precautionary Statements: | P280 | UN#: | N/A |
Hazard Statements: | H302-H312-H332 | Packing Group: | N/A |
GHS Pictogram: |
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Yield | Reaction Conditions | Operation in experiment |
---|---|---|
93% | With N-Bromosuccinimide In dichloromethane at 0 - 25℃; for 2 h; | 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, 93percent) 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 h; | 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, 86percent) as a white solid. ES/MS m/z (35C1,79Br) 245.9 (M+H). |
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