3-Chlorobenzaldehyde → HCID 22482074, compound

HRID 2182132Notes

Reaction equation

HRID 2182132 reaction equation
[NH2:1][C:2]1[CH:7]=[N:6][CH:5]=[C:4]([Cl:8])[N:3]=1.[Cl:9][C:10]1[CH:11]=[C:12]([CH:15]=[CH:16][CH:17]=1)[CH:13]=O.[BH4-].[Na+]>C1(C)C=CC=CC=1>[Cl:9][C:10]1[CH:11]=[C:12]([CH:15]=[CH:16][CH:17]=1)[CH2:13][NH:1][C:2]1[CH:7]=[N:6][CH:5]=[C:4]([Cl:8])[N:3]=1

Participants

5

Reactant 3

HCID 114773-ChlorobenzaldehydeHCID 1184582-Amino-6-ChloropyrazineHCID 4311764Sodium borohydride

Product 1

HCID 22482074HCID 22482074, compoundYield 36.3%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

To a solution of 2-amino-6-chloropyrazine (100 mg, 0.77 mmol) in 7.7 mL of anhydrous toluene was added 3-chlorobenzaldehyde (87.4 μL, 0.77 mmol) followed by 50 mg of activated, powdered 4 Å molecular sieves. The reaction was refluxed under nitrogen for 3 h, then cooled to ambient temperature and treated with sodium borohydride (43.0 mg, 1.16 mmol). The resultant slurry was heated to reflux under nitrogen overnight. After cooling to ambient temperature the reaction was filtered through a pad of Celite®, and the flitrate was concentrated in vacuo to a brown residue. Chromatography on a silica gel preparatory TLC plate (1:1 hexane:ethyl acetate) provided 71.0 mg of the title compound I-2a.

Workup

  1. temperatureThe reaction was refluxed under nitrogen for 3 h
  2. temperatureThe resultant slurry was heated
  3. temperatureto reflux under nitrogen overnight
  4. temperatureAfter cooling to ambient temperature the reaction
  5. filtrationwas filtered through a pad of Celite®
  6. concentrationthe flitrate was concentrated in vacuo to a brown residue

Sources & evidence

ORD record
ord-4b860727e6c54b11b96b33829e7c6fea
Source dataset
uspto-grants-2005_05
Patent number
US06894050B2

Reaction notes

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