Dimethylformamide → HCID 68622353, compound

HRID 1620071Notes

Reaction equation

C(=O)([O-])[O-].[Cs+].[Cs+].[NH:7]1[CH:11]=[CH:10][N:9]=[N:8]1.CN(C=O)C.Cl[C:18]1[CH:23]=[C:22]([NH2:24])[CH:21]=[CH:20][N:19]=1>O>[N:7]1[N:8]([C:18]2[CH:23]=[C:22]([NH2:24])[CH:21]=[CH:20][N:19]=2)[N:9]=[CH:10][CH:11]=1.[N:7]1([C:18]2[CH:23]=[C:22]([NH2:24])[CH:21]=[CH:20][N:19]=2)[CH:11]=[CH:10][N:9]=[N:8]1

Participants

Conditions

Temperature: 180 °C

Procedure

Cesium carbonate (1.9 g) and 1H-1,2,3-triazole (540 mg) were added to a tube containing a DMF (2 ml) solution containing 2-chloropyridin-4-amine (500 mg) and the tube was sealed, followed by stirring at 180° C. for 6 hours. Water was added to the reaction solution, followed by extraction with ethyl acetate. The resultant was washed with saturated saline and dried over anhydrous sodium sulfate. Subsequently, the solvent was distilled away under reduced pressure. The obtained residue was purified by silica gel chromatography (n-hexane:ethyl acetate=1:3 to 0:1), and a white solid of 2-(2H-1,2,3-triazol-2-yl)pyridin-4-amine (75.7 mg) and brown oily matter of 2-(1H-1,2,3-triazol-1-yl)pyridin-4-amine (25.1 mg) was thus obtained.

Workup

customthe tube was sealed
extractionfollowed by extraction with ethyl acetate
washThe resultant was washed with saturated saline
dry with materialdried over anhydrous sodium sulfate
distillationSubsequently, the solvent was distilled away under reduced pressure
customThe obtained residue was purified by silica gel chromatography (n-hexane:ethyl acetate=1:3 to 0:1)

Sources & evidence

ORD record: ord-aa3d022e1c774d878c66ab06e7e4d43d
Source dataset: uspto-grants-2014_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08772320B2

Reaction notes

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