Dimethylamine → HCID 67775541, compound

HRID 1802202Notes

Reaction equation

HRID 1802202 reaction equation
Br[C:2]1[N:11]=[C:5]2[CH:6]=[C:7]([Br:10])[CH:8]=[CH:9][N:4]2[N:3]=1.[CH3:12][NH:13][CH3:14]>>[Br:10][C:7]1[CH:8]=[CH:9][N:4]2[N:3]=[C:2]([N:13]([CH3:14])[CH3:12])[N:11]=[C:5]2[CH:6]=1

Participants

3

Reactant 2

HCID 674Dimethylamine2×HCID 677742742,7-Dibromo[1,2,4]triazolo[1,5-a]pyridine

Product 1

HCID 67775541HCID 67775541, compoundYield 72.3%

Procedure

A mixture of 2,7-dibromo-[1,2,4]triazolo[1,5-a]pyridine (2.16 g, 7.8 mmol) in dimethylamine (30% in EtOH, 60 ml, 355 mmol) is heated in 4 portions a ca. 540 mg/15 ml of dimethylamine in a high pressure vessel to 100° C. for 3 hours each. The batches are combined and the solvent evaporated. The light brown crude material (4.77 g) is loaded on silicagel and purified by chromatography on a 70 g silica column using heptane/ethyl acetate 10-40% as eluent affording 7-bromo-N,N-dimethyl-[1,2,4]triazolo[1,5-a]pyridin-2-amine (1.36 g, 72.3%) as a light yellow solid. Mp.: 133-4° C. MS: m/z=243.2 (M+H+).

Workup

  1. customthe solvent evaporated
  2. custompurified by chromatography on a 70 g silica column

Sources & evidence

ORD record
ord-dfeb67273b2a4140816fd8ec4b45b560
Source dataset
uspto-grants-2013_01
Patent number
US08349824B2

Reaction notes

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