| Identification | Back Directory | [Name]
1-(5-Pyrimidinyl)ethanone | [CAS]
10325-70-9 | [Synonyms]
5-Acetylpyrimidine
1-(Pyrimidin-5-yl)
5-EthanoylpyriMidine
5-Acetylpyrimidine 98%
1-(5-Pyrimidinyl)ethanone
1-(pyrimidin-5-yl)ethanone
Ethanone,1-(5-pyrimidinyl)-
1-(Pyrimidin-5-yl)ethan-1-one
Ethanone, 1-(5-pyrimidinyl)- (9CI)
1-(Pyrimidin-5-yl)ethan-1-one, 5-Ethanoylpyrimidine | [Molecular Formula]
C6H6N2O | [MDL Number]
MFCD09038477 | [MOL File]
10325-70-9.mol | [Molecular Weight]
122.12 |
| Chemical Properties | Back Directory | [Melting point ]
87-88 °C | [Boiling point ]
70 °C(Press: 2 Torr) | [density ]
1.136 | [Fp ]
92.1℃ | [storage temp. ]
Inert atmosphere,2-8°C | [form ]
solid | [pka]
1.03±0.10(Predicted) | [color ]
Pale yellow | [InChI]
InChI=1S/C6H6N2O/c1-5(9)6-2-7-4-8-3-6/h2-4H,1H3 | [InChIKey]
COTYNDRSENVEFI-UHFFFAOYSA-N | [SMILES]
C(=O)(C1=CN=CN=C1)C | [NIST Chemistry Reference]
5-Acetylpyrimidine(10325-70-9) |
| Hazard Information | Back Directory | [Uses]
5-Acetylpyrimidine is a substituted pyrimidine used in the study for prediction of relative potency of ketone protease inhibitors using molecular orbital theory.
| [Synthesis]
Step A: 5-Bromopyrimidine (3.18 g, 20 mmol) was dissolved in 50 mL of anhydrous tetrahydrofuran and cooled to -78 °C. 15mL of 1.6M n-butyllithium hexane solution was added slowly and dropwise with stirring. After maintaining the reaction at -78 °C for 30 min, anhydrous tetrahydrofuran solution (10 mL) of N-methoxy-N-methylacetamide (2.58 g, 25 mmol) was slowly added. The reaction was continued with stirring at -78 °C for 1 hour. Subsequently, the reaction mixture was slowly warmed to 0 °C and the reaction was quenched by the addition of saturated aqueous ammonium chloride solution. The reaction mixture was extracted with ethyl acetate (3 x 50 mL) and the organic phases were combined, washed with saturated brine and dried over anhydrous magnesium sulfate. After concentration under reduced pressure, the crude product was purified by silica gel column chromatography with 5% methanol/dichloromethane as eluent to give 1 g of 5-acetylpyrimidine (45% yield). Mass spectrometry (MS) showed a molecular ion peak (M+1) of 123.05. | [References]
[1] Patent: EP2385035, 2011, A1. Location in patent: Page/Page column 18-19
[2] Patent: CN103130792, 2016, B. Location in patent: Paragraph 0178-0180 |
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