Dimethylformamide → HCID 86634550, compound

HRID 81477Notes

Reaction equation

HRID 81477 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[C:3]([OH:7])[CH:2]=1.[H-].[Na+].Br[C:11]1[C:12](N)=[N:13][CH:14]=[C:15]([Br:17])[N:16]=1.C[N:20](C=O)C>>[Br:17][C:15]1[N:16]=[C:11]([NH2:20])[C:12]([O:7][C:3]2[CH:2]=[N:1][CH:6]=[CH:5][CH:4]=2)=[N:13][CH:14]=1

Participants

5

Reactant 4

HCID 6228DimethylformamideHCID 79713-HydroxypyridineHCID 24758Sodium hydrideHCID 6200042-Amino-3,5-dibromopyrazine

Product 1

HCID 86634550HCID 86634550, compound

Conditions

Temperature
170 °C

Procedure

A solution of pyridin-3-ol (0.045 g, 0.47 mmol), sodium hydride (12 m g, 0.47 mmol) in DMF (2 ml) is stirred at room temperature for 20 minutes. 3,5-Dibromo-pyrazin-2-ylamine (0.1 g, 0.39 mmol) is added and the reaction is heated at 170° C. for 15 minutes in a microwave. The solvent is concentrated in vacuo and the residue is purified using flash chromatography (SiO2, DCM/MeOH) to afford 6-bromo-3-(pyridin-3-yloxy)-pyrazin-2-ylamine. 1H NMR (400 MHz, DMSO-6) δ 8.53 (1H, d), 8.47 (1H, dd), 7.78 (1H, s), 7.75 (1H, dt), 7.51 (1H, dd), 6.89 (2H, s).

Workup

  1. concentrationThe solvent is concentrated in vacuo
  2. customthe residue is purified

Sources & evidence

ORD record
ord-99599a9394a4493aa55ef67497b82e1c
Source dataset
uspto-grants-2014_09
Patent number
US08846687B2

Reaction notes

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