ChemicalBook CAS DataBase List 8-METHOXY-2,4-DICHLOROQUINAZOLINE

8-METHOXY-2,4-DICHLOROQUINAZOLINE synthesis

7synthesis methods

Product Name:8-METHOXY-2,4-DICHLOROQUINAZOLINE
CAS Number:61948-59-2
Molecular formula:C9H6Cl2N2O
Molecular Weight:229.06

61948-86-5 Synthesis

61948-86-5
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$60.00/250mg

61948-59-2
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$43.00/100mg

Yield: 49%

Reaction Conditions:

Stage #1:5-methoxy-2,4-dioxo-1,2,3,4-tetrahydroquinazoline with N,N-dimethyl-aniline;trichlorophosphate for 4 h;Heating / reflux;
Stage #2: with sodium hydrogencarbonate in water

Steps:

To a flask charged with Intermediate 28 (310 mg, 1.6 mmol) was added phosphorous oxychloride (10 mL) followed by N,N-dimethylaniline (0.2 mL). Upon completion of addition, the reaction mixture was heated at reflux for 4h. The volatiles were then removed from the reaction mixture under reduced pressure to provide a residue. To the residue was added satd NaHCO₃ followed by EtOAc. The organic layer was separated, dried over Na₂SO₄ and filtered. The volatiles were removed under reduced pressure to provide another residue. This residue was subject to chromatography on silica gel eluting with 10 to 20% EtOAc/hexanes to provide Intermediate 29 as a white solid (180 mg, 49%). ¹H NMR (400 MHz, CDCl₃) δ ppm 4.03 (s, 3 H), 7.02 (d, J=8.35 Hz, 1 H), 7.55 (d, J=8.35 Hz, 1 H), 7.85 (t, J=8.35 Hz, 1 H).

References:

BRISTOL-MYERS SQUIBB COMPANY WO2007/30582, 2007, A2 Location in patent:Page/Page column 92