2,6-Lutidine → HCID 19436776, compound

HRID 1735015Notes

Reaction equation

HRID 1735015 reaction equation
[CH3:1][C:2]([Si:5]([CH3:14])([CH3:13])[C:6]1[CH:10]=[C:9]([OH:11])[N:8]([CH3:12])[N:7]=1)([CH3:4])[CH3:3].Cl[C:16]1[N:17]=[N:18][CH:19]=[C:20]([O:22][CH3:23])[CH:21]=1.N1C(C)=CC=CC=1C>C1(C)C(C)=CC=CC=1>[CH3:4][C:2]([Si:5]([CH3:14])([CH3:13])[C:6]1[CH:10]=[C:9]([O:11][C:16]2[N:17]=[N:18][CH:19]=[C:20]([O:22][CH3:23])[CH:21]=2)[N:8]([CH3:12])[N:7]=1)([CH3:1])[CH3:3]

Participants

5

Reactant 3

HCID 79372,6-LutidineHCID 109756123-Chloro-5-methoxypyridazineHCID 178481962HCID 178481962, compound

Product 1

HCID 19436776HCID 19436776, compoundYield 26%

Reagents, catalysts & solvents 1

HCID 7237O-XyleneSolvent

Procedure

3-[(1,1-Dimethylethyl)dimethylsilyl]-1-methyl-1H-pyrazol-5-ol (0.48 g, 0.0023 mole), 3-chloro-5-methoxypyridazine (0.36 g, 0.00249 mole) and 2,6-lutidine (0.396 mL, 0.003396 moles) were refluxed under N2 in xylene (20 mL) for 18 hours. The mixture was then filtered through silica gel with ethyl acetate and evaporated in vacuo. The crude compound was purified by reverse phase chromatography to give 3-[[3-[(1,1-dimethylethyl)dimethylsilyl]-1-methyl-1H-pyrazol-5-yl]oxy]-5-methoxypyridazine (0.19 g, 26% yield) as a brown solid.

Workup

  1. filtrationThe mixture was then filtered through silica gel with ethyl acetate
  2. customevaporated in vacuo
  3. customThe crude compound was purified by reverse phase chromatography

Sources & evidence

ORD record
ord-e4d9a82158314073beef3ce048b37d79
Source dataset
uspto-grants-1996_07
Patent number
US05536701

Reaction notes

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