[O:1]=[C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[C:9]([C:12]#[N:13])[CH:10]=2)[N:5]=[C:4]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[NH:3]1.C1COCC1.[BH4-].[Na+]>CO.O.[Co](Cl)Cl>[NH2:13][CH2:12][C:9]1[CH:10]=[C:11]2[C:6](=[CH:7][CH:8]=1)[N:5]=[C:4]([C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)[NH:3][C:2]2=[O:1]Prepared from INT-87. To a stirring solution of 4-oxo-2-phenyl-3,4-dihydroquinazoline-6-carbonitrile INT-87 (540 mg, 2.18 mmol) in MeOH (30 mL) and THF (10 mL) was added cobalt(II) chloride hydrate (646 mg, 4.37 mmol) and sodium borohydride (826 mg, 21.8 mmol) portionwise. After stirring at room temperature for 30 min the reaction mixture was quenched with 1 M HCl (5 mL) and filtered through a celite plug, washing with THF (50 mL). The mixture was diluted with EA (100 mL) and washed with NaHCO3 (120 mL) and brine (20 mL). The organics were dried over MgSO4 and concentrated in vacuo to afford 306 mg (56%) of 6-(aminomethyl)-2-phenylquinazolin-4(3H)-one INT-88 as a white powder. LCMS-ESI (m/z) calculated for C15H13N3O: 251; found 250 [M−H]−, tR=0.80 min (Method 10).
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