Reaction SMILES: Cl.Cl.Cl.Cl.Cl.[NH2:6][C:7]1[CH:12]=[CH:11][C:10]([C:13]2[CH:18]=[CH:17][N:16]=[C:15]([NH:19][C:20]3[CH:25]=[CH:24][C:23]([N:26]4[CH2:31][CH2:30][O:29][CH2:28][CH2:27]4)=[CH:22][CH:21]=3)[N:14]=2)=[CH:9][CH:8]=1.C(N(C(C)C)CC)(C)C.[C:41]([O:45][C:46]([N:48]1[CH2:52][CH2:51][CH2:50][C:49]1([CH3:56])[C:53](O)=[O:54])=[O:47])([CH3:44])([CH3:43])[CH3:42].F[P-](F)(F)(F)(F)F.N1(OC(N(C)C)=[N+](C)C)C2N=CC=CC=2N=N1>CC(N(C)C)=O>[CH3:56][C:49]1([C:53](=[O:54])[NH:6][C:7]2[CH:12]=[CH:11][C:10]([C:13]3[CH:18]=[CH:17][N:16]=[C:15]([NH:19][C:20]4[CH:21]=[CH:22][C:23]([N:26]5[CH2:27][CH2:28][O:29][CH2:30][CH2:31]5)=[CH:24][CH:25]=4)[N:14]=3)=[CH:9][CH:8]=2)[CH2:50][CH2:51][CH2:52][N:48]1[C:46]([O:45][C:41]([CH3:43])([CH3:42])[CH3:44])=[O:47]
Reactant: CC(C)(C)OC(=O)N1CCCC1(C)C(=O)O
Reactant: Nc1ccc(-c2ccnc(Nc3ccc(N4CCOCC4)cc3)n2)cc1
Agent: CN(C)C(On1nnc2cccnc21)=[N+](C)C
Agent: Cl
Agent: F[P-](F)(F)(F)(F)F
Solvent: CCN(C(C)C)C(C)C
Solvent: CC(=O)N(C)C
Product: CC(C)(C)OC(=O)N1CCCC1(C)C(=O)Nc1ccc(-c2ccnc(Nc3ccc(N4CCOCC4)cc3)n2)cc1
Temperature: 25 °C
Reaction time: 0.17 h
Yield: 27.3 %

Procedure:
An oven dried 50 ml round bottomed flask fitted with a Teflon stirrer and gas inlet was flushed with dry nitrogen and allowed to cool to room temperature. The flask was charged with 4-(4-aminophenyl)-N-(4-morpholinophenyl)pyrimidin-2-amine pentahydrochloride (1 equiv., 0.52 g, 0.9631 mmoles) and anhydrous dimethylacetamide (15 ml). The mixture was stirred for 10 minutes to allow for the complete dissolution of the amine. Diisoproplyethylamine (10 equiv., 1.24 g, 1.67 ml, 9.631 mmoles) was added in one lot and the reaction mixture was stirred for 5 minutes. 1-(tert-Butoxycarbonyl)-2-methylpyrrolidine-2-carboxylic acid (4 equiv., 3.852 mmoles, 0.883 g, purchased from Fluka-Sigma Aldrich) was added to the reaction mixture in one lot, followed by 2-(7-aza-1H-benzotriazole-1-yl)-1,1,3,3-tetramethyluronium hexafluorophosphate (HATU, 4 equiv., 3.852 mmoles, 1.464 g, purchased from Oakland Products). The reaction mixture was stirred at room temperature and the progress of the reaction was monitored by LC/MS. After 72 hours, the reaction mixture was quenched with ethyl acetate (20 ml), and transferred to separatory funnel. The reaction flask was further rinsed with ethyl acetate (20 ml), transferred to the separatory funnel, shaken and the layer separated off. The aqueous layer was further washed with ethyl acetate (3×50 ml). The combined ethyl acetate solutions were washed with cold water (2×50 ml) and saturated sodium chloride solution (2×50 ml). The ethyl acetate solution was dried over anhydrous sodium sulfate, filtered and evaporated under reduced pressure to give orange oil. The resulting crude-material was purified by silica phase flash chromatography (45 mm×250 mm) using 3:1 ethyl acetate-hexane to give 0.147 g of tert-butyl 2-methyl-2-(4-(2-(4-morpholinophenylamino)pyrimidin-4-yl)phenylcarbamoyl)-pyrrolidine-1-carboxylate as a white solid (27% yield). 1H NMR (400 MHz, d6-DMSO) 10.01 (br s, 1H), 9.45 (br s 1H), 8.19 (d, 1H), 7.70 (d, 2H), 7.46 (d, 2H), 6.74 (d, 1H), 6.66 (d, 2H), 6.28 (d, 2H), 3.67 (m, 4H), 3.40 (m, 1H), 3.30 (m, 1H), 2.29 (m, 4H), 1.76 (m, 1H), 1.64 (m, 1H), 1.58 (s, 3H), 1.54 (m, 1H), 1.40 (s, 9H). MS (EI) for C31H38N6O4: 559 (M+).