Dimethylformamide dimethyl acetal → HCID 89542360, compound

HRID 1024034Notes

Reaction equation

HRID 1024034 reaction equation
[Br:1][C:2]1[C:3]([NH2:9])=[N:4][CH:5]=[C:6]([Cl:8])[CH:7]=1.CO[CH:12](OC)[N:13]([CH3:15])[CH3:14]>O>[Br:1][C:2]1[C:3](/[N:9]=[CH:12]/[N:13]([CH3:15])[CH3:14])=[N:4][CH:5]=[C:6]([Cl:8])[CH:7]=1

Participants

4

Reactant 2

HCID 78373Dimethylformamide dimethyl acetalHCID 27639713-Bromo-5-chloropyridin-2-amine

Product 1

HCID 89542360HCID 89542360, compoundYield 63,483.801%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
100 °C

Procedure

A mixture of 3-bromo-5-chloropyridin-2-amine (10 g, 0.05 mol) and dimethoxy-N,N-dimethylmethanamine (7 g, 0.06 mmol) was stirred at 100° C. for 1 h. The mixture was poured into water and then extracted with Ethyl acetate (20 mL×4). The combined organic layer was concentrated under reduced pressure and the residue was purified with silica gel chromatography eluting with Ethyl acetate/PE (1:2) to afford 108a (10 g, 77%). LCMS: [M+H]+ 262.

Workup

  1. extractionextracted with Ethyl acetate (20 mL×4)
  2. concentrationThe combined organic layer was concentrated under reduced pressure
  3. customthe residue was purified with silica gel chromatography
  4. washeluting with Ethyl acetate/PE (1:2)

Sources & evidence

ORD record
ord-8f00ce4cc64142dca5d3c227b62cc6c3
Source dataset
uspto-grants-2014_05
Patent number
US08722676B2

Reaction notes

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