[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:9]([C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][C:21]=3[Cl:26])=[N:10][N:11]3[C:16]([O:17]CC)=[CH:15][CH:14]=[N:13][C:12]=23)=[CH:4][CH:3]=1.[OH-].C([N+](CCCC)(CCCC)CCCC)CCC.Cl>C1COCC1.C(OCC)(=O)C.O>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[C:9]([C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][C:21]=3[Cl:26])=[N:10][N:11]3[C:16]([OH:17])=[CH:15][CH:14]=[N:13][C:12]=23)=[CH:6][CH:7]=1
To a solution of 3-(4-chlorophenyl)-2-(2-chlorophenyl)-7-ethoxypyrazolo[1,5-a]pyrimidine (11A-1; 250 mg, 0.653 mmol) in THF (6.5 ml) was added water (1.5 ml) and 1M tetrabutylammonium hydroxide in water (3.3 ml, 3.3 mmol). The reaction was heated at 60° C. overnight, cooled, diluted with ethyl acetate and water, and then adjusted to pH 4.5 with 1M aqueous HCl. The aqueous layer was separated and extracted with ethyl acetate. The combined organic layers were washed with brine, dried (MgSO4), and then concentrated to afford, after trituration from ethyl acetate, I-12A-1a as a tan solid (138 mg, 60%): +APcI MS (M+1) 354.1; 1H NMR (400 MHz, CD3OD) δ 7.79 (d, J=7.1 Hz, 1H), 7.49–7.43 (m, 1H), 7.42–7.35 (m, 3H), 7.30 (d, J=8.7 Hz, 2H), 7.15 (d, J=8.7 Hz, 2H), 5.93 (d, J=7.1 Hz, 1H).
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