| Identification | Back Directory | [Name]
5-broMo-2-chloro-N-cyclopentylpyriMidin-4-aMine | [CAS]
733039-20-8 | [Synonyms]
5-broMo-2-chloro-N-cyclopentylpyriMidin-4-aMine
5-Bromo-2-chloro-4-(cyclopentylamino)pyrimidine
5-Bromo-2-chloro-N-cyclopentyl-4-pyrimidinamine
2-bromo-2-chloro-N-cyclopentylpyrimidin-4-amine
4-PyriMidinaMine, 5-broMo-2-chloro-N-cyclopentyl-
(5-Bromo-2-chloro-pyrimidin-4-yl)-cyclopentyl-amine
N-(5-Bromo-2-chloropyrimidin-4-yl)(cyclopentyl)amine
5-broMo-2-chloro-N-cyclopentylpyriMidin-4-aMine ISO 9001：2015 REACH | [EINECS(EC#)]
200-258-5 | [Molecular Formula]
C9H11BrClN3 | [MDL Number]
MFCD13181206 | [MOL File]
733039-20-8.mol | [Molecular Weight]
276.561 |
| Chemical Properties | Back Directory | [Boiling point ]
424.0±30.0 °C(Predicted) | [density ]
1.643±0.06 g/cm3(Predicted) | [storage temp. ]
Keep in dark place,Inert atmosphere,2-8°C | [form ]
solid | [pka]
1.22±0.10(Predicted) | [Appearance]
White to off-white Solid | [InChI]
InChI=1S/C9H11BrClN3/c10-7-5-12-9(11)14-8(7)13-6-3-1-2-4-6/h5-6H,1-4H2,(H,12,13,14) | [InChIKey]
DIVUXBABVYOIOT-UHFFFAOYSA-N | [SMILES]
C1(Cl)=NC=C(Br)C(NC2CCCC2)=N1 |
| Hazard Information | Back Directory | [Uses]
5-Bromo-2-chloro-N-cyclopentyl-4-pyrimidinamine is an intermediate in the preparation of 2-aminopyridines as cdk4 inhibitors for treating cell proliferative disorders. | [Synthesis]
5-Bromo-2,4-dichloropyrimidine (45.6 g, 200 mmol) was dissolved in dioxane (400 mL) at room temperature and subsequently cyclopentylamine (20.4 g, 240 mmol) was added to the solution. The reaction mixture was stirred continuously for 6 hours at room temperature. After completion of the reaction, the reaction mixture was diluted with ethyl acetate, washed sequentially with saturated brine and dried over anhydrous magnesium sulfate. The solvent was removed by concentration under reduced pressure to afford 5-bromo-2-chloro-N-cyclopentyl-4-pyrimidinamine as a light yellow solid (56 g, 100% yield), which could be used in subsequent reactions without further purification. The product was characterized as follows: 1H NMR (500 MHz, DMSO-d6) δ 8.23 (1H, s), 7.37 (1H, d, J = 7.3 Hz), 4.31 (1H, m), 1.92 (2H, m), 1.71 (2H, m), 1.53-1.59 (4H, m) ppm; LCMS-ESI (POS), m/z [M + H]+: measured value 276.0, calculated value 275.9. | [References]
[1] Patent: WO2009/85185, 2009, A1. Location in patent: Page/Page column 35
[2] Journal of Medicinal Chemistry, 2014, vol. 57, # 8, p. 3430 - 3449
[3] Combinatorial Chemistry and High Throughput Screening, 2017, vol. 20, # 8, p. 703 - 712
[4] Patent: WO2010/20675, 2010, A1. Location in patent: Page/Page column 89
[5] Patent: US2012/115878, 2012, A1. Location in patent: Page/Page column 5-6 |
|
|