[F:1][C:2]1[CH:3]=[N:4][C:5]([C@@H:8]([NH:10][C:11]2[N:16]=[C:15]([C:17](O)=[O:18])[C:14]([N+:20]([O-:22])=[O:21])=[C:13]([NH:23][C:24]3[CH:28]=[C:27]([CH3:29])[NH:26][N:25]=3)[N:12]=2)[CH3:9])=[N:6][CH:7]=1.CCN(C(C)C)C(C)C.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.[NH:63]1[CH2:68][CH2:67][O:66][CH2:65][CH2:64]1>CN(C=O)C.O.CCOC(C)=O>[F:1][C:2]1[CH:7]=[N:6][C:5]([C@@H:8]([NH:10][C:11]2[N:12]=[C:13]([NH:23][C:24]3[CH:28]=[C:27]([CH3:29])[NH:26][N:25]=3)[C:14]([N+:20]([O-:22])=[O:21])=[C:15]([C:17]([N:63]3[CH2:68][CH2:67][O:66][CH2:65][CH2:64]3)=[O:18])[N:16]=2)[CH3:9])=[N:4][CH:3]=1To a solution of 2-{[(1S)-1-(5-fluoropyrimidin-2-yl)ethyl]amino}-6-[(5-methyl-1H-pyrazol-3-yl)amino]-5-nitropyrimidine-4-carboxylic acid (Intermediate 50, 406 mg, ˜1 mmol), in DMF (5 ml) were added DIPEA (˜0.3 ml), HATU (456 mg) and morpholine (0.130 ml) at ambient temperature. The resulting mixture was stirred overnight. The mixture was diluted with H2O and EtOAc and the aqueous layer was extracted with EtOAc. The combined organic layers were washed with brine, saturated NaHCO3 (aq) solution, dried and evaporation of the volatiles under reduced pressure gave a colored residue. Purification by column chromatography (ISCO, 50%→70% EtOAc/hexanes) gave the title compound. LCMS: 473 [M+1].
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