Identification | Back Directory | [Name]
Methyl 2-(5-bromopyrimidin-2-yl)acetate | [CAS]
948594-80-7 | [Synonyms]
Methyl 2-(5-bromopyrimidin-2-yl) 6-(Boc-ami)-3-azabicyclo[3.1.1]heptane Methyl 2-(5-bromopyrimidin-2-yl)acetate 2-Pyrimidineacetic acid, 5-bromo-, methyl ester | [Molecular Formula]
C7H7BrN2O2 | [MDL Number]
MFCD16987768 | [MOL File]
948594-80-7.mol | [Molecular Weight]
231.05 |
Chemical Properties | Back Directory | [Boiling point ]
281.0±20.0 °C(Predicted) | [density ]
1.594±0.06 g/cm3(Predicted) | [storage temp. ]
Sealed in dry,Room Temperature | [pka]
-0.53±0.22(Predicted) | [Appearance]
Colorless to light yellow Liquid |
Hazard Information | Back Directory | [Synthesis]
Step 2: 1-tert-butyl 3-methyl 2-(5-bromopyrimidin-2-yl) malonate (1.88 g, crude) was dissolved in dichloromethane (20 mL). The mixture was cooled to 0 °C, followed by slow dropwise addition of 99% trifluoroacetic acid (10 mL). After the reaction mixture was brought to room temperature, stirring was continued for 4 hours. Upon completion of the reaction, the solvent was removed by distillation under reduced pressure. Toluene was added to the residue and the solution was evaporated to dryness. The residue was diluted with ethyl acetate and saturated sodium bicarbonate solution and partitioned. The organic layer was washed with brine, dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The crude product was purified by fast column chromatography on silica gel, using a gradient elution of heptane/ethyl acetate (100:0 to 60:40). Fractions containing the target product were collected, combined and concentrated under reduced pressure to give methyl 2-(5-bromopyrimidin-2-yl)acetate (405 mg, 34% yield, calculated in two steps) as a yellow oil. | [References]
[1] Patent: WO2018/138359, 2018, A1. Location in patent: Page/Page column 41; 64 [2] Patent: WO2007/99335, 2007, A1. Location in patent: Page/Page column 104 [3] Tetrahedron, 2009, vol. 65, # 4, p. 757 - 764 |
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