4-CHLORO-2-CHLOROMETHYLQUINAZOLINE synthesis

5synthesis methods

Product Name:4-CHLORO-2-CHLOROMETHYLQUINAZOLINE
CAS Number:34637-41-7
Molecular formula:C9H6Cl2N2
Molecular Weight:213.06

3817-05-8
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34637-41-7
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$180.00/1 G

Yield: 69%

Reaction Conditions:

Stage #1:2-(chloromethyl)quinazolin-4(3H)-one with N-ethyl-N,N-diisopropylamine;trichlorophosphate in toluene at 65;
Stage #2: with sodium hydrogencarbonate in water;toluene

Steps:

4; 45
A suspension of 2-chloromethyl-3H-quinazolin-4-one (12.27 g) in toluene (200 mL) was treated with Hünig's base (19 mL, 109 mmol) and POCl₃ (8.8 mL, 96.1 mmol) and heated to 65° C. overnight. The reaction was cooled to rt and the layers separated. The bottom layer was extracted with toluene. The top layers were combined and washed with cold H₂O and satd NaHCO₃, dried (MgSO₄), filtered and concentrated. Purification by gradient MPLC (SiO₂, 120 g column, EtOAc/hexanes, 0-100%) provided 9.72 g (69%) of the title compound as a white solid. ¹H NMR (DMSO-d₆) δ 8.33 (ddd, 1H), 8.05-8.22 (m, 2H), 7.93 (ddd, 1H), 4.97 (s, 2H); LC-MS (ESI⁺; 213 ([M+H]⁺).

References:

Myriad Pharmaceuticals, Inc. US2010/68197, 2010, A1 Location in patent:Page/Page column 7; 26

107-14-2 Synthesis