ChemicalBook CAS DataBase List 5-broMo-2-chloro-N-cyclopentylpyriMidin-4-aMine

5-broMo-2-chloro-N-cyclopentylpyriMidin-4-aMine synthesis

3synthesis methods

Product Name:5-broMo-2-chloro-N-cyclopentylpyriMidin-4-aMine
CAS Number:733039-20-8
Molecular formula:C9H11BrClN3
Molecular Weight:276.56

36082-50-5

1003-03-8

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

733039-20-8

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.

36082-50-5 Synthesis

36082-50-5
489 suppliers
$5.00/1g

1003-03-8 Synthesis

1003-03-8
236 suppliers
$10.00/1g

733039-20-8
277 suppliers
$6.00/1g

Yield:733039-20-8 100%

Reaction Conditions:

in 1,4-dioxane at 20; for 6 h;

Steps:

1

To a solution of 5-bromo-2,4- dichloropyrimidine (45.6 g, 200 mmol) in dioxane (400 mL) was added N-cyclopentylamine (20.4 g, 240 mmol) at room temperature. The mixture thus obtained was stirred at room temperature for 6 h. The reaction mixture was then diluted with ethyl acetate and washed with brine and dried over MgSO₄. The solvent was evaporated to give the title compound as a light yellow solid (56 g, 100%) which was used in next step without further purification. ¹H νMR (500 MHz, DMSO-d6) δ 8.23 (IH, s), 7.37 (IH, d, J=7.3 Hz), 4.31 (IH, m), 1.92 (2H, m), 1.71 (2H, m), 1.53-1.59 (4H, m) ppm; LCMS-ESI (POS), M/Z, M+l: Found 276.0, Calculated 275.9.

References:

WO2009/85185,2009,A1 Location in patent:Page/Page column 35

930-28-9 Synthesis