5-BROMO-2-PYRIMIDINEACETONITRILE synthesis
- Product Name:5-BROMO-2-PYRIMIDINEACETONITRILE
- CAS Number:831203-15-7
- Molecular formula:C6H4BrN3
- Molecular Weight:198.02
1305329-97-8
831203-15-7
To a solution of tert-butyl (5-bromopyrimidin-2-yl)-cyanoacetate (3.2 g, 10 mmol) in dichloromethane (30 mL) was added trifluoroacetic acid (10 mL). The reaction mixture was stirred at room temperature for 4 hours. After the reaction was complete, the mixture was concentrated. Water was added to the residue and the pH of the mixture was adjusted to neutral with saturated aqueous NaHCO3 solution. Subsequently, the mixture was extracted with ethyl acetate. After separation of the organic layer, the aqueous layer was again extracted with ethyl acetate. The organic layers were combined, washed sequentially with water and brine, dried over anhydrous MgSO4, filtered and concentrated. The residue was purified by column chromatography (eluent ratio: EtOAc/hexane = 1:3, 1:2, 1:1) to afford 5-bromo-2-pyrimidine acetonitrile as a white solid (1.2 g, 71% yield).
1305329-97-8
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Yield:831203-15-7 71%
Reaction Conditions:
Stage #1: tert-butyl 2-(5-bromopyrimidin-2-yl)-2-cyanoacetic acidwith trifluoroacetic acid in dichloromethane at 20; for 4 h;
Stage #2: with sodium hydrogencarbonate in water;
Steps:
26.B
To the solution of (5-bromo-pyrimidin-2-yl)-cyano-acetic acid tert-butyl ester (3.2 g, 10 mmol) in dichloromethane (30 mL) was added trifluoroacetic acid (10 mL). The reaction mixture was stirred at room temperature for 4 h. The mixture was concentrated. To the residue was added water, and the “pH” of the mixture was adjusted to neutral by saturated aqueous NaHCO3 solution. The mixture was then extracted with ethyl acetate. Organic layer was separated, the aqueous layer was extracted with ethyl acetate. The combined organic layers were washed with water, brine, dried over MgSO4, and concentrated. The residue was purified by chromatography (EtOAc:hexanes=1:3, 1:2, 1;1) to give (5-bromo-pyrimidin-2-yl)-acetonitrile as a white solid (1.2 g, 71%).
References:
US2011/118283,2011,A1 Location in patent:Page/Page column 14
65364-66-1
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