2-(Chloromethyl)pyrimidine → 2-{[4-(4-Phenyl-5-pyrimidin-4-yl-1H-imidazol-1-yl)piperidin-1-yl]methyl}pyrimidine
Reaction equation
C1(C2N=CN(C3CCNCC3)C=2C2C=CN=CN=2)C=CC=CC=1.ClCC1N=CC=CN=1.F[C:33]1[CH:38]=[CH:37][C:36]([C:39]2[N:40]=[CH:41][N:42]([CH:51]3[CH2:56][CH2:55][N:54]([CH2:57][C:58]4[N:63]=[CH:62][CH:61]=[CH:60][N:59]=4)[CH2:53][CH2:52]3)[C:43]=2[C:44]2[CH:49]=[CH:48][N:47]=[C:46](N)[N:45]=2)=[CH:35][CH:34]=1>>[C:36]1([C:39]2[N:40]=[CH:41][N:42]([CH:51]3[CH2:56][CH2:55][N:54]([CH2:57][C:58]4[N:63]=[CH:62][CH:61]=[CH:60][N:59]=4)[CH2:53][CH2:52]3)[C:43]=2[C:44]2[CH:49]=[CH:48][N:47]=[CH:46][N:45]=2)[CH:35]=[CH:34][CH:33]=[CH:38][CH:37]=1Participants
4
Reactant 3
Product 1
Procedure
The title product was prepared by reaction of 4-(4-phenyl-1-piperidin-4-yl-1H-imidazol-5-yl)pyrimidine (C23) with 2-(chloromethyl)pyrimidine according to the general procedure for the synthesis of 4-{4-(4-fluorophenyl)-1-[1-(pyrimidin-2-ylmethyl)piperidin-4-yl]-1H-imidazol-5-yl}pyrimidin-2-amine (3) in Example 3. In this case, after the reaction mixture was concentrated, the residue was partitioned between ethyl acetate and water. The organic layer was washed with saturated aqueous sodium chloride solution, dried over magnesium sulfate, filtered and concentrated under reduced pressure. Purification was effected via silica gel chromatography (Eluant: 25% methanol in ethyl acetate) to provide the product as a white solid. Yield: 63 mg, 0.16 mmol, 62%. APCI m/z 398.1 (M+1). 1H NMR (400 MHz, CDCl3) δ 2.11-2.20 (m, 4H), 2.23-2.32 (m, 2H), 3.13 (br d, J=12 Hz, 2H), 3.87 (s, 2H), 4.78 (tt, J=11, 4.5 Hz, 1H), 7.18 (dd, J=5.3, 1.5 Hz, 1H), 7.22 (t, J=4.9 Hz, 1H), 7.29-7.34 (m, 3H), 7.41-7.44 (m, 2H), 7.85 (s, 1H), 8.53 (br d, J=5.4 Hz, 1H), 8.76 (d, J=4.9 Hz, 2H), 9.29 (br d, J=1.5 Hz, 1H).