[CH:1]1([CH2:4][C:5](=O)/[C:6](/[C:11]2[CH:16]=[CH:15][N:14]=[C:13]([NH:17][C:18]3[CH:23]=[CH:22][N:21]=[CH:20][CH:19]=3)[N:12]=2)=[CH:7]\N(C)C)[CH2:3][CH2:2]1.Cl.[NH2:26][C:27]([NH2:29])=[NH:28].C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C>[CH:1]1([CH2:4][C:5]2[C:6]([C:11]3[CH:16]=[CH:15][N:14]=[C:13]([NH:17][C:18]4[CH:23]=[CH:22][N:21]=[CH:20][CH:19]=4)[N:12]=3)=[CH:7][N:26]=[C:27]([NH2:29])[N:28]=2)[CH2:3][CH2:2]1To a solution of (3Z)-1-cyclopropyl-4-(dimethylamino)-3-[2-(pyridin-4-ylamino)pyrimidin-4-yl]but-3-en-2-one (9) (80 mg, 0.247 mmol) in DMF (2061 μl), Guanidine HCl (35.3 mg, 0.371 mmol) and potassium carbonate (103 mg, 0.742 mmol) were added and the reaction was heated at 60° C. for 4 hours. The crude product was purified by reverse-phase HPLC [30-90% organic phase over 15 minutes] followed by Biotage™ silica gel chromatography [10 g SNAP column, 100% DCM to 12% MeOH/DCM] to obtain the desired product as a white solid (24.72 mg, 31.3% yield). 1H NMR (400 MHz, MeOD) δ ppm 0.01-0.14 (m, 2H) 0.39 (q, J=6.06 Hz, 2H) 0.94-1.10 (m, 1H) 2.87 (d, J=7.07 Hz, 2H) 7.10 (d, J=5.05 Hz, 1H) 7.83 (d, J=6.57 Hz, 2H) 8.30 (d, J=6.57 Hz, 2H) 8.41 (s, 1H) 8.57 (d, J=5.05 Hz, 1H). HRMS (ES+) for C17H17N7.H+ [MH+]: calcd, 320.1624; found, 320.1636. UV-LC: 100% UV purity at 254/214 nm; tR=4.67 minute over 7.75 minutes.
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