Reaction SMILES: [Cl:1][C:2]1[CH:11]=[C:10]2[C:5]([C:6](=[O:25])[N:7]([CH3:24])[C:8]([CH2:12][N:13]3[CH2:18][CH2:17][N:16]([CH2:19][CH2:20][OH:21])[CH2:15][CH:14]3CC)=[N:9]2)=[CH:4][C:3]=1[CH2:26][N:27]([C:31]1[CH:43]=[CH:42][C:34]([C:35]([O:37]C(C)(C)C)=O)=[CH:33][CH:32]=1)[CH2:28][C:29]#[CH:30].[NH2:44][CH2:45][C:46]1[CH:47]=[N:48][CH:49]=[CH:50][CH:51]=1.C1CN([P+](ON2N=NC3C=CC=CC2=3)(N2CCCC2)N2CCCC2)CC1.F[P-](F)(F)(F)(F)F.C(N(C(C)C)CC)(C)C.Cl.[OH-].[Na+]>ClCCl.FC(F)(F)C(O)=O.CN(C=O)C.O>[Cl:1][C:2]1[CH:11]=[C:10]2[C:5]([C:6](=[O:25])[N:7]([CH3:24])[C:8]([CH2:12][N:13]3[CH2:14][CH2:15][N:16]([CH2:19][CH2:20][OH:21])[CH2:17][CH2:18]3)=[N:9]2)=[CH:4][C:3]=1[CH2:26][N:27]([C:31]1[CH:43]=[CH:42][C:34]([C:35]([NH:44][CH2:45][C:46]2[CH:47]=[N:48][CH:49]=[CH:50][CH:51]=2)=[O:37])=[CH:33][CH:32]=1)[CH2:28][C:29]#[CH:30]
Reactant: NCc1cccnc1
Reactant: C#CCN(Cc1cc2c(=O)n(C)c(CN3CCN(CCO)CC3CC)nc2cc1Cl)c1ccc(C(=O)OC(C)(C)C)cc1
Agent: Cl
Agent: F[P-](F)(F)(F)(F)F
Agent: [Na+]
Solvent: O=C(O)C(F)(F)F
Solvent: O
Solvent: ClCCl
Product: C#CCN(Cc1cc2c(=O)n(C)c(CN3CCN(CCO)CC3)nc2cc1Cl)c1ccc(C(=O)NCc2cccnc2)cc1
Temperature: 0 °C
Reaction time: 0.08 h

Procedure:
A solution of tert-butyl 4-[N-[7-chloro-3-methyl-2-(4-(2-hydroxyethyl)ethyl-piperazin-1-yl)methyl-4-oxo-3,4-dihydroquinazolin-6-ylmethyl]-N-(prop-2-ynyl)amino]benzoate (0.157 g, 0.27 mmol) (Preparation Example 21) in dichloromethane (1.6 ml) and trifluoroacetic acid (2.6 ml) was stirred at room temperature for 55 min with protection from the light. The trifluoroacetic acid was then removed in vacuo, and the residue was treated with dichloromethane/toluene, concentrated in vacuo to leave an orange glass which was dried in vacuo over P2O5 (0.114 g). This was dissolved in anhydrous DMF (2.5 ml) under argon. The solution was placed in an ice-bath and then a solution of 3-(aminomethyl)pyridine (0.043 g, 0.40 mmol) in anhydrous DMF (1.5 ml) was added followed by PyBOP® (0.147 g, 0.28 mmol), and.finally diisopropylethylamine (0.209 g, 1.62 mmol). The solution was stirred at 0° C. for 5 min, then the ice-bath was removed and stirring was continued under argon for 3 h. The clear solution was then partitioned between ethyl acetate (200 ml) and saturated aqueous sodium bicarbonate (100 ml). The organic layer was washed with more saturated aqueous sodium bicarbonate (100 ml), brine (100 ml), dried (Na2SO4) and concentrated in vacuo. Purification by column chromatography, on gradient elution with methanol in dichloromethane (5 to 15%), afforded a glass. This was suspended in water (6 ml) and the pH was first adjusted to 1 with 1N aqueous HCl to give a clear solution, then to ˜9 with 1N NaOH; a pale yellow precipitate was obtained. The solid was collected by filtration, washed with water, and dried in vacuo over P2O5 (6.065 g, 40%), mp 115-117° C.; 1H-NMR (DMSO-d6) 2.35 (t obscured, J=6.3 Hz, 2H, NCH2CH2OH), 2.38, 2.46 (2×br s, 8H, N(CH2CH2)2), 3.18 (s, 1H, C≡CH), 3.46 (q, J=6.1 Hz, 2H, NCH2CH2OH), 3.60 (s, 5H, N3-Me, 2-CH2), 4.26 (t, J=5.3 Hz, 1H, NCH2CH2 OH), 4.36 (d, J=1.8 Hz, 2H, CH2C≡C), 4.45 (d, J=5.8 Hz, 2H, CONHCH2), 4.77 (s, 2H, 6-CH2), 6.79 (d, J=8.9 Hz, 2H, 3,5′-ArH), 7.33 (dd, J=4.8, 7.8 Hz, 1H, pyr 5-H), 7.69 (dt, J=1.8, 7.8 Hz, pyr 4-H), 7.76 (d, J=8.8 Hz, 2H, 2′,6′-ArH), 7.80, 7.91 (2×s, 2H, 5-H, 8-H), 8.43 (dd, J=1.6, 4.8 Hz, 1H, pyr 6-H), 8.52 (s, 1H, 2-H pyr), 8.72 (t, J=5.8 Hz, 1H, CONH).