Cyclohexylamine → HCID 25241920, compound
Reaction equation
[CH:1]1([NH2:7])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.Cl[C:9]1[N:14]=[C:13]([N:15]2[C:19]3[CH:20]=[CH:21][CH:22]=[CH:23][C:18]=3[N:17]=[N:16]2)[C:12]([Cl:24])=[CH:11][N:10]=1>C1COCC1>[N:15]1([C:13]2[C:12]([Cl:24])=[CH:11][N:10]=[C:9]([NH:7][CH:1]3[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]3)[N:14]=2)[C:19]2[CH:20]=[CH:21][CH:22]=[CH:23][C:18]=2[N:17]=[N:16]1Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
Cyclohexylamine (0.21 mL, 1.88 mmol) was added in portions to a solution of 1-(2,5-dichloro-pyrimidin-4-yl)-1H-benzotriazole (250 mg, 0.94 mmol) in THF (30 mL) at RT under nitrogen atmosphere. The resultant colorless solution was stirred at RT for 4 hours. TEA (2.82 mmol) was then added and the reaction mixture was stirred at RT overnight. The mixture was partitioned between water (50 mL) and EtOAc (50 mL). The organic layer was separated, washed twice with water (50 mL) and once with brine (50 mL), then dried over Na2SO4, filtered and evaporated under reduced pressure to give an off-white solid. This crude material was purified via flash chromatography (toluene/EtOAc, 98/2) to afford 162 mg (53% yield) of (4-benzotriazol-1-yl-5-chloro-pyrimidin-2-yl)-cyclohexyl-amine as an off-white solid. MS: 329.14 (M+1)+, 301.14 ((M+1)+−28).