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CAS No. : | 1234616-70-6 | MDL No. : | MFCD17015892 |
Formula : | C7H2BrCl2N3 | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | VPAHKVLQMKEPQW-UHFFFAOYSA-N |
M.W : | 278.92 | Pubchem ID : | 72207616 |
Synonyms : |
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Signal Word: | Warning | Class: | N/A |
Precautionary Statements: | P261-P305+P351+P338 | UN#: | N/A |
Hazard Statements: | H302-H315-H319-H335 | Packing Group: | N/A |
GHS Pictogram: |
* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
80% | With trichlorophosphate; In N,N-dimethyl-formamide; for 6.0h;Reflux; | General procedure: 2,4,6-Trichloro-pyrido[2,3-d]pyrimidine (6) (C7H2Cl3N3): A mixture of 50 mL of POCl3, two drops of DMF, and 5 g of 6-chloro-1H-pyrido[2,3-d]pyrimidine-2,4-dione 4 were heated to reflux. After 6 h, the reaction was evaporated under reduced pressure; 400 mL of CH2Cl2 and 20 mL of water were added to the residue at C. The aqueous phase was extracted, the organic layers were combined and then dried over magnesium sulfate. After filtration the filtrate was evaporated under reduced pressure, and then washed with Et2O to obtain compound 6 as a yellow solid in 64% yield. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
64% | With N,N-diethylaniline; trichlorophosphate; at 110.0℃; for 5.0h; | Prepared from13 (1.02?g, 4.23?mmol) by general procedure C. Yellow solid (755.1?mg, 64%). 1H NMR (CDCl3) delta?=?8.75 (d, 1H, J?=?2.5?Hz), 9.30 (d, 1H, J?=?2.5?Hz). MS (ESI) 279.8 (M+H)+. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
100% | With N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; at 20.0℃; for 3.0h; | Prepared from 17 (155.7?mg, 0.558?mmol) and N-Boc-cis-1,4-cyclohexanediamine (144?mg, 0.670?mmol) by general procedure D. Slight yellow solid (275.0?mg, quant.). 1H NMR (CDCl3) delta?=?1.46 (s, 9H), 1.87 (m, 8H), 3.71 (m, 1H), 4.43 (m, 1H), 4.64 (br, 1H), 6.09 (br, 1H), 8.26 (d, 1H, J?=?2.4?Hz), 9.02 (d, 1H, J?=?2.4?Hz). MS (ESI) 456.0 (M+H)+. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
76% | With tetrakis(triphenylphosphine) palladium(0); potassium carbonate; In toluene; at 110.0℃; for 3.0h; | General procedure: To an argon degassed solution of 6-halogeno-2,4-dichloropyrido[2,3-d]pyrimidine 6 or 7 (0.5 mmol) in toluene (6mL) the desired (Het)aryl boronic acid was added then (1.5 equiv)potassium carbonate and (0.05 equiv) Pd(PPh3)4 were also added.The reaction was stirred at 110C for the desired time. After completion of the reaction, 10 mL of water was added, and then extracted with dichloromethane (3 10 mL), the organic layers were combined and dried using magnesium sulfate, and the solvent was evaporated under reduced pressure. The obtained material was purified on silica gel by column chromatography (CH2Cl2/PE: 90/10)to afford compounds 8-12. 2,4-Dichloro-6-(4-methoxyphenyl)pyrido[2,3-d]pyrimidine (8) (C14H9Cl2N3O): Compound 8 was obtained from 2,4,6-trichloropyrido[2,3-d]pyrimidine 6 using 4-methoxyphenyl boronic acid (1.05 equiv), as a white solid in 83%yield. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
36%; 7% | With tetrakis(triphenylphosphine) palladium(0); potassium carbonate; In toluene; at 110.0℃; for 3.0h; | General procedure: To an argon degassed solution of 6-halogeno-2,4-dichloropyrido[2,3-d]pyrimidine 6 or 7 (0.5 mmol) in toluene (6mL) the desired (Het)aryl boronic acid was added then (1.5 equiv)potassium carbonate and (0.05 equiv) Pd(PPh3)4 were also added.The reaction was stirred at 110C for the desired time. After completion of the reaction, 10 mL of water was added, and then extracted with dichloromethane (3 10 mL), the organic layers were combined and dried using magnesium sulfate, and the solvent was evaporated under reduced pressure. The obtained material was purified on silica gel by column chromatography (CH2Cl2/PE: 90/10)to afford compounds 8-12. 2,4-Dichloro-6-(4-methoxyphenyl)pyrido[2,3-d]pyrimidine (8) (C14H9Cl2N3O): Compound 8 was obtained from 2,4,6-trichloropyrido[2,3-d]pyrimidine 6 using 4-methoxyphenyl boronic acid (1.05 equiv), as a white solid in 83%yield. |