5-broMo-2-chloro-N-cyclopentylpyriMidin-4-aMine Chemical Properties

Boiling point:

424.0±30.0 °C(Predicted)

Density 

1.643±0.06 g/cm3(Predicted)

storage temp. 

under inert gas (nitrogen or Argon) at 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

Safety Information

Hazard Codes 

T

Risk Statements 

25

Safety Statements 

45

5-broMo-2-chloro-N-cyclopentylpyriMidin-4-aMine Usage And Synthesis

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

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