[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:16]3[C:11](=[N:12][CH:13]=[N:14][C:15]=3[NH2:17])[N:10]([CH:18]([CH3:20])[CH3:19])[N:9]=2)=[CH:4][C:3]=1[O:21][CH3:22].C([O-])([O-])=O.[K+].[K+].Br[CH2:30][CH2:31][CH2:32][OH:33]>CN(C=O)C>[NH2:17][C:15]1[N:14]=[CH:13][N:12]=[C:11]2[N:10]([CH:18]([CH3:19])[CH3:20])[N:9]=[C:8]([C:5]3[CH:6]=[CH:7][C:2]([NH:1][CH:31]([CH3:30])[CH2:32][OH:33])=[C:3]([O:21][CH3:22])[CH:4]=3)[C:16]=123-(4-amino-3-methoxyphenyl)-1-isopropyl-1H-pyrazolo[3,4-d]pyrimidin-4-amine (BA20d) (30 mg, 0.10 mmol) was dissolved in DMF (0.400 ml). K2CO3 (55 mg, 0.4 mmol) was added and reaction was stirred at 70° C. 3-bromo-1-propanol (0.050 ml, 0.6 mmol) was added and reaction was stirred overnight. Solid K2CO3 was removed by filtration. Solvent was partially removed in vacuo. Sodium citrate (50 ml) was added and reaction was extracted with saturated NaCl and CH2Cl2. Organic phases concentrated in vacuo and purified by RP-HPLC (MeCN:H2O:0.1% TFA) to yield BA99 (8.4 mg, 24% yield). ESI-MS (M+H)+ m/z calcd 357.2, found 357.1.
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