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][O: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][O:16][CH2:17][CH2:18]3)=[N:9]2)=[CH:4][C:3]=1[CH2:21][N:22]([C:26]1[CH:38]=[CH:37][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:28][CH:27]=1)[CH2:23][C:24]#[CH:25]
Reactant: NCc1cccnc1
Reactant: C#CCN(Cc1cc2c(=O)n(C)c(CN3CCOCC3)nc2cc1Cl)c1ccc(C(=O)OC(C)(C)C)cc1
Agent: F[P-](F)(F)(F)(F)F
Agent: c1ccc2c(c1)nnn2O[P+](N1CCCC1)(N1CCCC1)N1CCCC1
Solvent: ClCCl
Solvent: CCN(C(C)C)C(C)C
Solvent: O=C(O)C(F)(F)F
Product: C#CCN(Cc1cc2c(=O)n(C)c(CN3CCOCC3)nc2cc1Cl)c1ccc(C(=O)NCc2cccnc2)cc1
Temperature: 25 °C
Reaction time: 3 h

Procedure:
A solution of tert-butyl 4-[N-[7-chloro-3-methyl-2-morpholinomethyl-4-oxo-3,4-dihydroquinazolin-6-ylmethyl]-N-(prop-2-ynyl)amino]benzoate (Preparation Example 17) (0.093 g, 0.173 mmol) in dichloromethane (1.2 ml) and trifluoroacetic acid (1.6 ml) was stirred at room temperature for 55 min. The solution was then concentrated in vacuo to an oily residue which was treated with toluene/dichloromethane. The solvents were then removed in vacuo and the residue was dried in vacuo over P2O5 to afford a pale yellow solid. This was dissolved in DMF (1.2 ml) under argon and the solution was placed in an ice-bath. A solution of 3-(aminomethyl)pyridine (0.028 g, 0.26 mmol) in anhydrous DMF (0.2 ml) was then added followed by PyBOP® (0.094 g, 0.182 mmol) and diisopropylethylamine (0.133 g, 1.03 mmol). After 5 min the ice-bath was removed and the reaction mixture was stirred at room temperature for an additional 3 h under argon. The 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 and concentrated in vacuo to an oily residue which was purified by column chromatography using a gradient of methanol in dichloromethane (2 to 5%) as eluant. The white solid was triturated with dichloromethane/hexanes (v/v, 1/1). The white solid was collected by filtration, washed with hexanes and dried in vacuo over P2O5 (0.066 g, 67%), mp>145° C. (it softens). 1H-NMR (DMSO-d6) 2.55 (br s obscured, 4H, morpholine CH2NCH2), 3.19 (s, 1H, C≡CH), 3.56 (s(poorly resolved triplet), 4H, morpholine CH2OCH2), 3.63 (s, 3H, N3-Me), 3.71 (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=8.0 Hz, 1H, pyr 4-H), 7.75 (d, J=8.7 Hz, 2H, 2′,6′-ArH), 7.79, 7.93 (2×s, 2H, 5-H, 8-H), 8.43 (d, J=3.4 Hz, 1H, pyr 6-H), 8.52 (s, 1H, pyr 2-H), 8.72 (t, J=5.9 Hz, 1H, CONH), MS (ESI, m/z) 571, 573 [(M+H)+, 62%, 22% respectively; Cl isotopic pattern]. FAB-HRMS measured: 571.2240; calculated for C31H32ClN6O3 (M+H)+ 571.2224.