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2-Amino-5-bromopyridine → 6-Bromo-2-methyl-[1,2,4]triazolo[1,5-a]pyridine

HRID 1907338
Notes
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Reaction equation

HRID 1907338 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([Br:8])=[CH:4][N:3]=1.CO[C:11](OC)([N:13]([CH3:15])[CH3:14])[CH3:12]>CN(C)C=O>[Br:8][C:5]1[CH:6]=[CH:7][C:2]2[N:3]([N:13]=[C:11]([CH3:12])[N:1]=2)[CH:4]=1.[Br:8][C:5]1[CH:6]=[CH:7][C:2]([N:1]=[C:11]([N:13]([CH3:15])[CH3:14])[CH3:12])=[N:3][CH:4]=1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 2

HCID 706222-Amino-5-bromopyridineHCID 878351,1-Dimethoxyethyl(dimethyl)amine

Product 2

HCID 6111916-Bromo-2-methyl-[1,2,4]triazolo[1,5-a]pyridineHCID 66746222HCID 66746222, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
130 °C

Procedure

To a stirred solution of 2-amino-5-bromopyridine (1.73 g, 10 mmol) in N,N-dimethylformamide (20 mL) was added dimethylacetamide dimethylacetal (3.99 g, 30 mmol). The reaction mixture was heated to 130° C. overnight. After cooling to room temperature, the volatiles were removed under reduced pressure to afford the desired product N′-(5-bromo-pyridin-2-yl)-N,N-dimethyl-acetamidine as a brown oil.

Workup

  1. temperatureAfter cooling to room temperature
  2. customthe volatiles were removed under reduced pressure

Sources & evidence

ORD record
ord-b817a87e2c7b4092b7cd2961a03eab0e
Source dataset
uspto-grants-2013_12
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08598163B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes