[CH3:1][N:2]1[C:7](=[O:8])[C:6]2=[C:9]([NH:25][C:26]3[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=3)[N:10]([CH2:12][C:13]3[CH:18]=[CH:17][C:16]([C:19]4[CH:24]=[CH:23][CH:22]=[CH:21][N:20]=4)=[CH:15][CH:14]=3)[N:11]=[C:5]2[N:4]([CH2:32][CH:33]2[CH2:37][CH2:36][CH2:35][NH:34]2)[C:3]1=[O:38].C=O.[BH3-][C:42]#N.[Na+]>CO>[CH3:1][N:2]1[C:7](=[O:8])[C:6]2=[C:9]([NH:25][C:26]3[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=3)[N:10]([CH2:12][C:13]3[CH:18]=[CH:17][C:16]([C:19]4[CH:24]=[CH:23][CH:22]=[CH:21][N:20]=4)=[CH:15][CH:14]=3)[N:11]=[C:5]2[N:4]([CH2:32][CH:33]2[CH2:37][CH2:36][CH2:35][N:34]2[CH3:42])[C:3]1=[O:38]5-methyl-3-(phenylamino)-2-(4-(pyridin-2-yl)benzyl)-7-(pyrrolidin-2-ylmethyl)-2H-pyrazolo[3,4-d]pyrimidine-4,6(5H,7H)-dione is dissolved in CH3OH (200 μL), and then 37% formaldehyde (2.3 μL) is added at room temperature. After 5 min, NaBH3CN (1.8 mg, 0.028 mmol) in CH3OH (100 μL) is added. The reaction mixture is stirred at r.t. for 30 min. The mixture is purified by HPLC to give pure product as white solids. MS (ESI) m/z 522.3 [M+H]+.
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