Reaction SMILES: [Cl:1][C:2]1[CH:11]=[C:10]2[C:5]([C:6](=[O:20])[N:7]([CH3:19])[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[CH2:21][N:22]([C:26]1[CH:38]=[CH:37][C:29]([C:30]([O:32]C(C)(C)C)=O)=[CH:28][CH:27]=1)[CH2:23][C:24]#[CH:25].[NH2:39][CH2:40][C:41]1[CH:42]=[N:43][CH:44]=[CH:45][CH:46]=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>ClCCl.FC(F)(F)C(O)=O.CN(C=O)C>[Cl:1][C:2]1[CH:11]=[C:10]2[C:5]([C:6](=[O:20])[N:7]([CH3:19])[C:8]([CH2:12][N:13]3[CH2:14][CH2:15][CH2:16][CH2:17][CH2:18]3)=[N:9]2)=[CH:4][C:3]=1[CH2:21][N:22]([C:26]1[CH:27]=[CH:28][C:29]([C:30]([NH:39][CH2:40][C:41]2[CH:42]=[N:43][CH:44]=[CH:45][CH:46]=2)=[O:32])=[CH:37][CH:38]=1)[CH2:23][C:24]#[CH:25]
Reactant: C#CCN(Cc1cc2c(=O)n(C)c(CN3CCCCC3)nc2cc1Cl)c1ccc(C(=O)OC(C)(C)C)cc1
Reactant: NCc1cccnc1
Agent: F[P-](F)(F)(F)(F)F
Agent: c1ccc2c(c1)nnn2O[P+](N1CCCC1)(N1CCCC1)N1CCCC1
Solvent: CCN(C(C)C)C(C)C
Solvent: O=C(O)C(F)(F)F
Solvent: CN(C)C=O
Product: C#CCN(Cc1cc2c(=O)n(C)c(CN3CCCCC3)nc2cc1Cl)c1ccc(C(=O)NCc2cccnc2)cc1
Reaction time: 0.05 h

Procedure:
A solution of tert-butyl 4-[N-[7-chloro-3-methyl-4-oxo-2-piperidinomethyl-3,4-dihydroquinazolin-6-ylmethyl]-N-(prop-2-ynyl)amino]benzoate (Preparation Example 16) (0.086 g, 0.16 mmol) in dichloromethane (1.2 ml) and trifluoroacetic acid (1.6 ml) was stirred at room temperature for 55 min with protection from the light. The solvents were then removed in vacuo and the residue was treated with toluene/dichloromethane; concentrated in vacuo and the residue was dried in vacuo over P2O5. This solid was dissolved in anhydrous DMF (1.2 ml) under argon and the solution was placed in an ice-bath. A solution of 3-(aminomethyl)pyridine (0.026 g, 0.24 mmol) in DMF (0.2 ml) was then added followed by PyBOP® (0.087 g, 0.168 mmol) and diisopropylethylamine (0.123 g, 0.96 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 h at room temperature before being partitioned between ethyl acetate (200 ml) and saturated aqueous bicarbonate (100 ml). The organic layer was washed with more saturated aqueous bicarbonate (100 ml) and brine (100 ml), dried (Na2SO4) and concentrated in vacuo. The residue was purified by column chromatography using 3% methanol in dichloromethane as eluant, then triturated with 20% dichloromethane in hexanes to give a white solid which was collected by filtration, washed with hexanes and dried in vacuo over P2O5 (0.072 g, 79%), mp 148-150° C.; 1H-NMR (DMSO-d6) 1.48 (br s, 6H, piperidine CH2CH2CH2), 2.43 (br s, 4H, piperidine CH2NCH2), 3.18 (s, 1H, C≡CH), 3.61 (s, 3H, N3-Me), 3.57 (s, 2H, 2-CH2), 4.36 (s, 2H, CH2C≡C), 4.45 (d, J=5.7 Hz, 2H, CONHCH2), 4.77 (s, 2H, 6-CH2), 6.79 (d, J=8.8 Hz, 2H, 3,5′-ArH), 7.32 (dd, J=4.8, 7.8 Hz, 1H, pyr 5-H), 7.68 (d, J=7.7 Hz, 1H, pyr 4-H), 7.76 (d, J=8.7 Hz, 2H, 2′,6′-ArH), 7.79, 7.93 (2×s, 2H, 5-H, 8-H), 8.43 (d, J=3.6 Hz, 1H, pyr 6-H), 8.52 (s, 1H, pyr 2-H), 8.73 (t, J=5.9 Hz, 1H, CONH).; MS (FAB, m/z) 569,571 [(M+H)+, 100%, 40% respectively; Cl isotopic pattern]. FAB-HRMS: measured 569.2403; calculated for C32H34ClN6O2 (M+H)+: 569.2432.