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| | 5-Bromo-2-chloropyrimidine Basic information |
| | 5-Bromo-2-chloropyrimidine Chemical Properties |
| Melting point | 73-79 °C (lit.) | | Boiling point | 95°C 15mm | | density | 1.859±0.06 g/cm3(Predicted) | | Fp | 95°C/15mm | | storage temp. | Keep in dark place,Sealed in dry,Room Temperature | | solubility | soluble in Methanol | | pka | -2.84±0.22(Predicted) | | form | Crystalline Powder | | color | Off-white to beige | | Water Solubility | insoluble | | BRN | 507955 | | Stability: | Hygroscopic | | InChI | InChI=1S/C4H2BrClN2/c5-3-1-7-4(6)8-2-3/h1-2H | | InChIKey | XPGIBDJXEVAVTO-UHFFFAOYSA-N | | SMILES | C1(Cl)=NC=C(Br)C=N1 | | CAS DataBase Reference | 32779-36-5(CAS DataBase Reference) |
| Hazard Codes | Xi | | Risk Statements | 36/37/38 | | Safety Statements | 26-36/39-37/39-36 | | RIDADR | UN 3335 | | WGK Germany | 3 | | HazardClass | IRRITANT | | HS Code | 29335990 |
| | 5-Bromo-2-chloropyrimidine Usage And Synthesis |
| Description | 5-Bromo-2-chloropyrimidine is a halogenated pyrimidine analogue containing chloro and bromo substituents at positions 2 and 5 of the benzene ring structure. The compound is used as a pharmaceutical intermediate in the preparation of macitentan, an endothelin receptor antagonist drug for the treatment of pulmonary hypertension. | | Chemical Properties | Off-white to beige crystalline powder | | Uses | 5-Bromo-2-chloropyrimidine is applied as a pharmaceutical intermediate, in the synthesis of pharmaceutical goods such as inhibitors. It is also employed in the cross-coupling reactions of indium organometallics with 2,5-dihalopyrimidines. | | Uses | 5-Bromo-2-chloropyrimidine is a intermediate in the synthesis of pharmaceutical goods such as inhibitors. | | Preparation | Under nitrogen protection, 35 g (0.2 mol) of 2-hydroxy-5-bromopyrimidine, 61.3 g (0.4 mol) of phosphorus oxychloride, and 200 mL of toluene were added into the reaction flask. At 35 ℃, triethylamine 40.5g was added and then heated up at 80-85 ℃. Stir the reaction for 6 hours, sampling HPLC to detect the raw material (less than 2%), and lower the temperature. After concentrating the mixture under reduced pressure to remove most of the toluene and Phosphorus oxychloride, put the reaction solution into 10°C water, and adjust pH=8-9 with 20% sodium carbonate aqueous solution. Finally, 5-Bromo-2-chloropyrimidine was obtained after purification. | | Reactivity Profile | 5-Bromo-2-chloropyrimidine, a 2,5-dihalopyrimidine, is a useful organic electrophiles. It could react with tri(3-indolyl)indium reagent through cross-coupling reaction. Other aryl- and heteroarylindium
reagents, such as thiophenyl-, pyridyl-, naphthyl-, and
alkynylindium reagents, also reacted with 5-bromo-2-
chloropyrimidine to afford the corresponding 2-chloro-5-substituted pyrimidines[1].
 | | References | [1] Mosquera A, et al. Cross-Coupling Reactions of Indium Organometallics with 2,5-Dihalopyrimidines: Synthesis of Hyrtinadine A?. Organic Letters, 2008; 10: 3745–3748.
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| | 5-Bromo-2-chloropyrimidine Preparation Products And Raw materials |
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