Potassium Carbonate → [4-(2-Chloro-benzimidazol-1-yl)-[1,3,5]triazin-2-yl]-(3,4,5-trimethoxy-phenyl)amine

HRID 983447Notes

Reaction equation

Cl[C:2]1[N:7]=[CH:6][N:5]=[C:4]([NH:8][C:9]2[CH:14]=[C:13]([O:15][CH3:16])[C:12]([O:17][CH3:18])=[C:11]([O:19][CH3:20])[CH:10]=2)[N:3]=1.[Cl:21][C:22]1[NH:23][C:24]2[CH:30]=[CH:29][CH:28]=[CH:27][C:25]=2[N:26]=1.C([O-])([O-])=O.[K+].[K+]>C(C#N)(C)=O>[Cl:21][C:22]1[N:26]([C:2]2[N:7]=[CH:6][N:5]=[C:4]([NH:8][C:9]3[CH:14]=[C:13]([O:15][CH3:16])[C:12]([O:17][CH3:18])=[C:11]([O:19][CH3:20])[CH:10]=3)[N:3]=2)[C:25]2[CH:27]=[CH:28][CH:29]=[CH:30][C:24]=2[N:23]=1

Participants

Conditions

Temperature: 65 °C

Procedure

To a suspension of (4-chloro-[1,3,5]triazin-2-yl)-(3,4,5-trimethoxy-phenyl)amine (2.97 g, 10 mmol) and 2-chlorobenzimidazole (1.53 g, 10 mmol) in dry AcCN (100 mL) was added ground K2CO3 (1.68 g, 12 mmol). The resulting mixture was heated at 65° C. for 4 h, cooled to RT, concentrated in vacuo and purified by column chromatography (EtOAc/n-Hexanes) to provide [4-(2-chloro-benzimidazol-1-yl)-[1,3,5]triazin-2-yl]-(3,4,5-trimethoxy-phenyl)amine as a white powder. MS m/z 413=[M+H]+. Calc'd for C19H17ClN6O3: 412.11:

Workup

temperaturecooled to RT
concentrationconcentrated in vacuo
custompurified by column chromatography (EtOAc/n-Hexanes)

Sources & evidence

ORD record: ord-c5907bfa13a3406ca05f5868b6dc4931
Source dataset: uspto-grants-2005_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06864255B2

Reaction notes

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