3-Hydroxypyridine → HCID 51037725, compound

HRID 1045811Notes

Reaction equation

HRID 1045811 reaction equation
Cl[C:2]1[CH:7]=[N:6][CH:5]=[C:4]([Cl:8])[N:3]=1.[OH:9][C:10]1[CH:11]=[N:12][CH:13]=[CH:14][CH:15]=1.C([O-])([O-])=O.[K+].[K+]>CN(C=O)C.CCOC(C)=O>[Cl:8][C:4]1[CH:5]=[N:6][CH:7]=[C:2]([O:9][C:10]2[CH:11]=[N:12][CH:13]=[CH:14][CH:15]=2)[N:3]=1

Participants

6

Reactant 3

HCID 79713-HydroxypyridineHCID 11430Potassium CarbonateHCID 785042,6-Dichloropyrazine

Product 1

HCID 51037725HCID 51037725, compoundYield 93.5%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
150 °C

Procedure

2,6-Dichloropyrazine (1.0 g, 6.7 mmol, 1.0 eq), 3-hydroxypyridine (638 mg, 6.71 mmol, 1.00 eq) and K2CO3 (1.11 g, 8.03 mmol, 1.20 eq) were dissolved in DMF (10 mL) and heated in a microwave for 15 minutes at 150° C. The reaction was cooled, diluted with EtOAc and washed with H2O (3×). The organic layer was dried (MgSO4), filtered and concentrated in vacuo. Purification by flash chromatography on silica gel afforded 1.3 g (93%) of the title compound as a white solid: 1H NMR (400 MHz, CDCl3) δ 8.59 (d, J=2.3 Hz, 1H), 8.56 (d, J=4.4 Hz, 1H), 8.41 (s, 1H), 8.37 (s, 1H), 7.71 (dq, J=8.4, 1.3 Hz, 1H), 7.51 (dd, J=8.4, 4.9 Hz, 1H); ES-MS [M+1]+: 208.1.

Workup

  1. temperatureThe reaction was cooled
  2. washwashed with H2O (3×)
  3. dry with materialThe organic layer was dried (MgSO4)
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customPurification by flash chromatography on silica gel

Sources & evidence

ORD record
ord-b18039655b1a42efb55089d74a05aa45
Source dataset
uspto-grants-2013_10
Patent number
US08569308B2

Reaction notes

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