Reaction SMILES: [Cl:1][C:2]1[CH:11]=[C:10]2[C:5]([C:6](=[O:27])[N:7]([CH2:19][C:20](=[O:26])[N:21]([CH2:24][CH3:25])[CH2:22][CH3:23])[C:8]([CH2:12][N:13]3[CH2:18][CH2:17][CH2:16][CH2:15][CH2:14]3)=[N:9]2)=[CH:4][C:3]=1[CH2:28][N:29]([C:33]1[CH:45]=[CH:44][C:36]([C:37]([O:39]C(C)(C)C)=O)=[CH:35][CH:34]=1)[CH2:30][C:31]#[CH:32].[NH2:46][CH2:47][C:48]1[CH:49]=[N:50][CH:51]=[CH:52][CH:53]=1.C1CN([P+](ON2N=NC3C=CC=CC2=3)(N2CCCC2)N2CCCC2)CC1.F[P-](F)(F)(F)(F)F.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:27])[N:7]([CH2:19][C:20](=[O:26])[N:21]([CH2:22][CH3:23])[CH2:24][CH3:25])[C:8]([CH2:12][N:13]3[CH2:18][CH2:17][CH2:16][CH2:15][CH2:14]3)=[N:9]2)=[CH:4][C:3]=1[CH2:28][N:29]([C:33]1[CH:34]=[CH:35][C:36]([C:37]([NH:46][CH2:47][C:48]2[CH:49]=[N:50][CH:51]=[CH:52][CH:53]=2)=[O:39])=[CH:44][CH:45]=1)[CH2:30][C:31]#[CH:32]
Reactant: NCc1cccnc1
Reactant: C#CCN(Cc1cc2c(=O)n(CC(=O)N(CC)CC)c(CN3CCCCC3)nc2cc1Cl)c1ccc(C(=O)OC(C)(C)C)cc1
Agent: Cl
Agent: F[P-](F)(F)(F)(F)F
Agent: [Na+]
Solvent: O
Solvent: ClCCl
Solvent: O=C(O)C(F)(F)F
Product: C#CCN(Cc1cc2c(=O)n(CC(=O)N(CC)CC)c(CN3CCCCC3)nc2cc1Cl)c1ccc(C(=O)NCc2cccnc2)cc1
Reaction time: 0.05 h

Procedure:
A solution of tert-butyl 4-[N-[7-chloro-3-diethylcarbamoylmethyl-4-oxo-2-(piperidin-1-yl)methyl-3,4-dihydroquinazolin-6-ylmethyl]-N-(prop-2-ynyl)amino]benzoate (0.065 g, 0.10 mmol) (Preparation Example 29) in dichloromethane (1 ml) and trifluoroacetic acid (1.3 ml) was stirred at room temperature for 1 hour with protection from the light. The solvent was then removed in vacuo and the remainder was treated with toluene/dichloromethane, concentrated in vacuo and the residue was dried in vacuo over P2O5. This material was dissolved in anhydrous DMF (1.3 ml) under argon and the solution was placed in.an ice-bath. A solution of 3-(aminomethyl)pyridine (0.016 g, 0.15 mmol) in DMF (0.3 ml) was then added followed by PyBOP® (0.055 g, 0.10 mmol) and diusopropylethylamine (0.077 g, 0.60 mmol). Stirring was continued at 0° C. for 3 min; then the ice-bath was removed and the reaction mixture was stirred for an additional 3 hours before being partitioned between ethyl acetate (100 ml) and saturated aqueous bicarbonate (80 ml). The aqueous layer was extracted with more ethyl acetate (2×50 ml). The combined organic extracts were washed With brine (80 ml), dried (Na2SO4) and concentrated in vacuo. The residue was purified by column chromatography using a gradient of methanol in dichloromethane (2 to 5%). The product was reprecipitated from dichloromethane/hexanes to give a white solid. This was suspended in water (5 ml) and the pH was first adjusted to ˜1 with 1N HCl, then to ˜11 with 1N NaOH; a white precipitate was obtained. This was collected by filtration , washed with water and dried in vacuo over P2O5 (0.040 g, 60%), mp>105° C.; 1H-NMR (DMSO-d6), 1.00, 1.18 (2×t, 6H, 2×CH2CH3), 1.40 (br s, 6H, piperidine CH2CH2CH2), 2.32 (br s, 4H, piperidine CH2NCH2), 3.24, 3.40 (2×q obscured by water peak, 4H, 2×CH2CH3), 4.37 (s, 2H, CH2C≡C), 4.43 (d, J=5.6 Hz, 2H, CONHCH2), 4.77 (s, 2H, 6-CH2), 5.10 (s, 2H, N3—CH2), 6.77 (d, J=8.8 Hz, 2H, 3,5′-ArH), 7.31 (dd, J=4.8, 7.8 Hz, 1H, pyr 5-H), 7.67 (d, J=7.8 Hz, 1H, pyr 4-H), 7.73 (d, J=8.6 Hz, 2H, 2′,6′-ArH), 7.83, 7.86 (2×s, 2H, 5-H, 8-H), 8.42 (d, J=3.2 Hz, 1H pyr 6-H), 8.52 (s, 1H, pyr 2-H), 8.73 (t, J=5.6 Hz, 1H, CONH).; MS (ESI, m/z) 668, 670 [(M+H)+, 100%, 37% respectively; Cl isotopic pattern].