Potassium Carbonate → (4-Chloro-[1,3,5]triazin-2-yl)-(2-phenyl-cyclopropyl)amine
Reaction equation
Cl[C:2]1[N:7]=[C:6]([Cl:8])[N:5]=[CH:4][N:3]=1.C([O-])([O-])=O.[K+].[K+].Cl.[C:16]1([C@@H:22]2[CH2:24][C@H:23]2[NH2:25])[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1>>[Cl:8][C:6]1[N:5]=[CH:4][N:3]=[C:2]([NH:25][CH:23]2[CH2:24][CH:22]2[C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[N:7]=1Participants
4
Conditions
- Temperature
- 0 °C
Procedure
A mixture of 2,4-dichloro-1,3,5-triazine (0.5 g, 3.34 mmol) and solid K2CO3 (2.3 g, 16.7 mmol) was suspended in ACCN (20 mL) under nitrogen at 0° C. followed by addition of trans-2-phenylcyclopropylamine hydrochloride (566 mg, 3.34 mmol). The mixture was stirred at 0° C. for 1.25 h. The reaction was quenched by pouring onto ice/water. The white solid formed was collected by suction filtration. The solid was dissolved into EtOAc (100 mL), washed with brine, dried over Na2SO4, concentrated under reduced pressure then purified by column chromatography (elution with 1:1 EtOAc/hexanes followed by EtOAc) to give (4-chloro-[1,3,5]triazin-2-yl)-(2-phenyl-cyclopropyl)amine.
Workup
- customwas suspended in ACCN (20 mL) under nitrogen at 0° C.
- customThe reaction was quenched
- additionby pouring onto ice/water
- customThe white solid formed
- filtrationwas collected by suction filtration
- dissolutionThe solid was dissolved into EtOAc (100 mL)
- washwashed with brine
- dry with materialdried over Na2SO4
- concentrationconcentrated under reduced pressure
- customthen purified by column chromatography (elution with 1:1 EtOAc/hexanes followed by EtOAc)
Sources & evidence
- ORD record
- ord-aecbbfa5393e473da29b0cb9e88b1ef1
- Source dataset
- uspto-grants-2005_04
- Patent number
- US06881737B2
Reaction notes
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