| Identification | More | [Name]
5-Bromopyrimidine-2-carbonitrile | [CAS]
38275-57-9 | [Synonyms]
5-BROMO-2-CYANOPYRIMIDINE
5-BROMOPYRIMIDINE-2-CARBONITRILE
5-Bromopyrimidine-2-carbonitrile95%
2-Cyano-5-bromopyrimidine
2-PYRIMIDINECARBONITRILE, 5-BROMO- | [Molecular Formula]
C5H2BrN3 | [MDL Number]
MFCD02940446 | [Molecular Weight]
183.99 | [MOL File]
38275-57-9.mol |
| Chemical Properties | Back Directory | [Boiling point ]
317.7±34.0 °C(Predicted) | [density ]
1.86±0.1 g/cm3(Predicted) | [storage temp. ]
Inert atmosphere,2-8°C | [form ]
Solid | [pka]
-4.65±0.22(Predicted) | [color ]
White to yellow | [Water Solubility ]
Slightly soluble in water. | [Sensitive ]
Moisture Sensitive | [InChI]
InChI=1S/C5H2BrN3/c6-4-2-8-5(1-7)9-3-4/h2-3H | [InChIKey]
VPQICCOHFSGBMA-UHFFFAOYSA-N | [SMILES]
C1(C#N)=NC=C(Br)C=N1 | [CAS DataBase Reference]
38275-57-9(CAS DataBase Reference) |
| Hazard Information | Back Directory | [Chemical Properties]
Light?yellow?crystalline?powder | [Uses]
5-Bromo-2-cyanopyrimidine is an important raw material and intermediate used in organic synthesis, pharmaceuticals and agrochemicals. | [Preparation]
5-Bromopyrimidine-2-carbonitrile is a pharmaceutical intermediate that can be obtained by reacting 5-bromo-2-chloropyrimidine with potassium nitride. It can also be obtained as follow: 5-Bromo-2-chloropyrimidine (7.51 g, 38.83 mmol), dissolved in DMSO (20 mL), is added to a mixture of NaCN (1.9 g, 38.83 mmol) and l,4-diazabicyclo[2,2,2]octane (0.87 g, 7.77 mmol) in DMSO (10 mL) and water (20 mL). The mixture is stirred overnight, and then water (100 mL) is added. The mixture is extracted with ether (3x100 mL). The combined organic layer is dried (Na2SO4), filtered, and concentrated in vacuo to afford 5-Bromopyrimidine-2-carbonitrile as a solid.
 | [Synthesis]
General procedure for the synthesis of 5-bromo-2-cyanopyrimidine from sodium cyanide and 5-bromo-2-chloropyrimidine:
1. In a reaction flask, 5-bromo-2-chloropyrimidine (10 g, 51.8 mmol) was dissolved in dimethyl sulfoxide (26 mL).
2. a mixture of sodium cyanide (2.59 g, 51.8 mmol) and triethylenediamine (1.2 g, 10.4 mmol) in dimethyl sulfoxide (14 mL) and water (28 mL) was added sequentially to the above solution.
3. The reaction mixture was stirred at room temperature for 18 hours.
4. Upon completion of the reaction, the mixture was diluted with water (130 mL) and extracted with ether (3 x 150 mL).
5. The organic phases were combined, dried over anhydrous sodium sulfate and concentrated under reduced pressure to give a light yellow solid.
6. The resulting solid was purified by recrystallization from hot dichloromethane to afford the target product 5-bromo-2-cyanopyrimidine.
Yield: 99% (9.4 g).
1H NMR (CDCl3, 400 MHz) δ: 8.84 (s, 2H). | [References]
[1] Patent: WO2005/28452, 2005, A1. Location in patent: Page/Page column 87
[2] Patent: WO2008/121670, 2008, A1. Location in patent: Page/Page column 93-94
[3] Patent: WO2008/57336, 2008, A2. Location in patent: Page/Page column 44
[4] Patent: WO2004/56369, 2004, A1. Location in patent: Page/Page column 20 |
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