반응 #72653

반응 방정식

NaOH

2-chloro-N-methylquinazolin-4-amine

2-Chloro-N-methylquinazolin-4-amine

thiourea

formic acid

→

title compound

수율 18.1%

4-(Methylamino)quinazoline-2(1H)-thione

수율 18.1%

용매

ethanol

반응 조건

후처리

1. 1
   온도was refluxed for 1.5 h
2. 2
   기타The solvent was removed under vacuum
3. 3
   기타the residue was purified by preparative HPLC
4. 4
   세척eluting with acetonitrile and water

실험 절차

A mixture of 2-chloro-N-methylquinazolin-4-amine (Example 39) (100 mg, 0.52 mmol), thiourea (47.5 mg, 0.62 mmol) and formic acid (0.02 mL, 0.52 mmol) in ethanol (5 mL) was refluxed for 1.5 h. After cooling to room temperature, the reaction mixture was neutralized with diluted NaOH aqueous solution. The solvent was removed under vacuum and the residue was purified by preparative HPLC eluting with acetonitrile and water to give the title compound (18 mg, 18%). 1H NMR (400 MHz, DMSO-d6) δ2.99 (d, J=4.8 Hz, 3H), 7.25 (t, J=7.6 Hz, 1H), 7.35 (d, J=8.0 Hz, 1H), 7.65-7.61 (m, 1H), 8.0 (d, J=8.0 Hz, 1H), 8.70 (d, J=4.4 Hz, 1H), 12.32 (s, 1H). MS 192 (MH+).

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