5-BROMO-2-PYRIMIDINEACETONITRILE

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 NaHCOA mixture of tert-butyl 2- (5-bromopyrimidin-2-yl) -2-cyanoacetic acid tert-butyl ester (3.068, 10.301111111), 4111001 /Of hydrochloric acid (20 mL) and acetic acid (20 mL)Followed by adding to 100 mL of the reaction flask, The reaction was warmed to 70 ° (2 hours to stop the reaction, the reaction solution was poured directly into ice water (150 mL)Ethyl acetate (50 mL X 3). The organic phases were combined, washed successively with water (50 mL X 3) and saturated brine (50 mL), dried over anhydrous sodium sulfate, and the solvent was distilled off under reduced pressure. The resulting crude product was directly subjected to silica gel column The title compound (yellow solid, 1.37 g, 67.40percent) was obtained by chromatography and purification (petroleum ether / ethyl acetate (ν / ν) = 5/1)Synthesis of(5-bromopyrιmιdιn-2-yl)acetomtrιleTo 2 7Og of ethyl (5-bromopyπmidin-2-yl)(cyano)acetate (9 970 mmol) in dimethylsulfoxyde (20 ml) was added 0 584g of sodium chloride (9 970 mmol) and 0 18mL of water (9 970 mmol) The mixture was heated at 120Synthesis of(5-bromopyrimidin-2-yl)acetonitrileTo 2.7Og of ethyl (5-bromopyrimidin-2-yl)(cyano)acetate (9.970 mmol) in dimethylsulfoxyde (20 ml) was added 0.584g of sodium chloride (9.970 mmol) and 0.18mL of water (9.970 mmol). The mixture was heated at 120To a suspension of sodium hydride (53 mg (60percent oil suspension), 1.34 mmol) in DMSO (2 ml) at room temperature under a nitrogen atmosphere was added tert-butyl cyanoacetate (197 mg, 39 mmol) in DMSO (1 ml) was added dropwise over 15 minutes and then stirred at room temperature for 1 hour.5-Bromo-2-chloropyrimidine (100 mg, 0.52 mmol) was added to the reaction solution, and the mixture was stirred at room temperature for 8 hours. Next, a saturated aqueous solution of ammonium chloride was added to the reaction system, extracted with ethyl acetate, washed with water, and then concentrated under reduced pressure to obtain a crude product.Subsequently, trifluoroacetic acid (1.8 ml) was added to a solution of the dried crude product in dichloromethane (2.3 ml) at 0 ° C., and the mixture was stirred for 1 hour and then allowed to warm to room temperature and stirred for 15 hours did.The reaction solution was neutralized with a saturated aqueous sodium hydrogen carbonate solution, extracted with ethyl acetate, washed with water and saturated brine, and dried over anhydrous sodium sulfate. The anhydrous sodium sulfate was filtered and concentrated under reduced pressure to obtain a crude product of (5-bromopyrimidin-2-yl) acetonitrile.The obtained crude product was purified by silica gel column chromatography (hexane: ethyl acetate = 3: 1) to obtain (5-bromopyrimidin-2-yl) acetonitrile. Yield 46 mg, yield 45percent, white solid.

Molecular Weight:198.02
XLogP3:0.6
Hydrogen Bond Acceptor Count:3
Rotatable Bond Count:1
Exact Mass:196.95886
Monoisotopic Mass:196.95886
Topological Polar Surface Area:49.6
Heavy Atom Count:10
Complexity:142
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes