2,4-Dichloro-1,3,5-triazine → HCID 22560109, compound

HRID 983432Notes

Reaction equation

Cl[C:2]1[N:7]=[C:6]([Cl:8])[N:5]=[CH:4][N:3]=1.CCN(C(C)C)C(C)C.[N:18]1([CH2:23][C:24]2[CH:25]=[C:26]([NH2:30])[CH:27]=[CH:28][CH:29]=2)[CH:22]=[CH:21][N:20]=[N:19]1>CN(C=O)C.CCOC(C)=O.O>[Cl:8][C:6]1[N:5]=[CH:4][N:3]=[C:2]([NH:30][C:26]2[CH:27]=[CH:28][CH:29]=[C:24]([CH2:23][N:18]3[CH:22]=[CH:21][N:20]=[N:19]3)[CH:25]=2)[N:7]=1

Participants

Conditions

Temperature: 0 °C

Procedure

2,4-Dichloro-1,3,5-triazine (405.8 mg, 2.7065 mmol) is dissolved in DMF (2 ml). To the stirring solution cooled to 0° C. is added DIEA (471 μl, 2.7065 mmol). This solution is added dropwise to a 0° C. mix of DMF (2 ml) and 3-[1,2,3]triazol-1-ylmethyl-phenylamine (471.5 mg, 2.7065 mmol). The reaction is stirred at 0° C. for 15 minutes to 40 minutes and then at RT for 20 minutes to 2 hours. The mixture is diluted with EtOAc and water. The layers are separated, and the aqueous layer is extracted twice with EtOAc. The combined organic layer is washed 3 times with brine, dried over Na2SO4, and concentrated under reduced pressure, giving (4-chloro-[1,3,5]triazin-2-yl)-(3-[1,2,3]triazol-1-ylmethyl-phenyl)amine as a white foam.

Workup

additionThis solution is added dropwise to a 0° C.
waitat RT for 20 minutes to 2 hours
customThe layers are separated
extractionthe aqueous layer is extracted twice with EtOAc
washThe combined organic layer is washed 3 times with brine
dry with materialdried over Na2SO4
concentrationconcentrated under reduced pressure

Sources & evidence

ORD record: ord-d3d3e304c4c642a5ae9f21b5e6665919
Source dataset: uspto-grants-2005_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06864255B2

Reaction notes

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