Sodium hydride → 3-Chloro-6-(3-methyl-5-pyridin-2-yl-3H-[1,2,3]triazol-4-ylmethoxy)-pyridazine

HRID 402403Notes

Reaction equation

HRID 402403 reaction equation
[H-].[Na+].[CH3:3][N:4]1[C:8]([CH2:9][OH:10])=[C:7]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][N:12]=2)[N:6]=[N:5]1.[Cl:17][C:18]1[N:19]=[N:20][C:21](Cl)=[CH:22][CH:23]=1>C1COCC1>[Cl:17][C:18]1[N:19]=[N:20][C:21]([O:10][CH2:9][C:8]2[N:4]([CH3:3])[N:5]=[N:6][C:7]=2[C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][N:12]=2)=[CH:22][CH:23]=1

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 673313,6-DichloropyridazineHCID 67498007(3-methyl-5-pyridin-2-yl-3H-[1,2,3]triazol-4-yl)-methanol

Product 1

HCID 573350973-Chloro-6-(3-methyl-5-pyridin-2-yl-3H-[1,2,3]triazol-4-ylmethoxy)-pyridazineYield 99.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent3×

Procedure

To a suspension of sodium hydride (55%, 92 mg, 2.10 mmol) in THF (3 mL) was added a solution of (3-methyl-5-pyridin-2-yl-3H-[1,2,3]triazol-4-yl)-methanol (400 mg, 2.103 mmol) in THF (5 mL) under ice cooling. The mixture was then allowed to warm up to room temperature and stirred for 30 min. Again under ice cooling was added a solution of 3,6-dichloropyridazine (315 mg, 2.10 mmol) in THF (5 mL) and the resulting mixture stirred at room temperature for 16 h. The mixture was then poured into ice water and extracted with ethyl acetate and the combined organic extracts washed with brine, dried over sodium sulphate, filtered and evaporated. Purification by chromatography (silica, 0 to 50% ethyl acetate in heptane) afforded the title compound (630 mg, 99%) as a white solid. MS: m/e=303.0 [M+H]+.

Workup

  1. stirringthe resulting mixture stirred at room temperature for 16 h
  2. extractionextracted with ethyl acetate
  3. washthe combined organic extracts washed with brine
  4. dry with materialdried over sodium sulphate
  5. filtrationfiltered
  6. customevaporated
  7. customPurification by chromatography (silica, 0 to 50% ethyl acetate in heptane)

Sources & evidence

ORD record
ord-8aeeaff01a9549d0ae35fa71bc34faa7
Source dataset
uspto-grants-2014_06
Patent number
US08742097B2

Reaction notes

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