Methyl iodide → Quinazolin-2-ylhydrazine
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C[N:2]1[CH2:11][C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[NH:4][C:3]1=S.CI.O.[NH2:16][NH2:17]>CCOCC.C(O)C.O>[NH:16]([C:3]1[N:2]=[CH:11][C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[N:4]=1)[NH2:17]C[N:2]1[CH2:11][C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[NH:4][C:3]1=S.CI.O.[NH2:16][NH2:17]>CCOCC.C(O)C.O>[NH:16]([C:3]1[N:2]=[CH:11][C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[N:4]=1)[NH2:17]A mixture of 3-methyl-1,2,3,4-tetrahydroquinazolin-2-thione (5.87 g., prepared as described in J. Pharm. Sci., 1961, 50, 866), methyl iodide (6 ml) and ethanol (230 ml) was refluxed for 1 hour, cooled and diluted with ether. The precipitate (8.27g) was suspended in ethanol (42 ml), treated with hydrazine hydrate (42 ml) and the mixture refluxed for 1 hour, cooled, diluted with water and extracted with chloroform. The extracts were washed, dried and evaporated to give the 2-hydrazinoquinazoline (4.55g). This was dissolved in a mixture of 2N hydrochloric acid (27 ml.) and acetic acid (13 ml), cooled, and treated, dropwise below 5°, with a solution of sodium nitrite (2.04 g) in water (13 ml). The mixture was allowed to stand for a further hour at room temperature, basified with 10N sodium hydroxide solution and the precipitate filtered off and dried. Recrystallization from methanol gave the title compound (1.25 g., m.p. 134°-5° ).
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