ChemicalBook CAS DataBase List 8-BROMO-2-CHLOROQUINAZOLINE

8-BROMO-2-CHLOROQUINAZOLINE synthesis

5synthesis methods

Product Name:8-BROMO-2-CHLOROQUINAZOLINE
CAS Number:956100-63-3
Molecular formula:C8H4BrClN2
Molecular Weight:243.49

956100-62-2 Synthesis

956100-62-2
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$27.00/1g

956100-63-3
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$55.00/250mg

Yield: 67%

Reaction Conditions:

with isopentyl nitrite in tetrahydrofuran at 60; for 8.67 h;

Steps:

L; 195d
To a stirred mixture of 8-bromo-2-chloroquinazolin-4-amine (12.93 g, 50 mmol) in THF (500 mL) was added isoamyl nitrite (23.43 g, 200 mmol) over 3 hours and 40 mins at 6O⁰C. The mixture was stirred for another 5 hours. TLC (PE:EA,1 :1) showed reaction complete. After cooling to room temperature, the solvent was stripped and the residue was taken into DCM (300 mL). The organic layer was washed with brine (100 mL), water (100 mL), then dried over anhydrous Na₂SO₄ and purified by chromatography (DCM:PE, 1:1) to give the title compound as a yellow solid ( 8.21 g, 67%). 1 HNMR (DMSOd₆, 400 MHz): δ 9.66 (s, 1 H), 8.45 (dd, J = 0.8, 7.6 Hz, 1 H), 8.26 (dd, J = 0.8, 8.0 Hz, 7.73 (dd, J = 7.6, 8.0 Hz, 1 H).

References:

PFIZER PRODUCTS INC. WO2007/125405, 2007, A2 Location in patent:Page/Page column 25; 81-82