Sodium hydride → HCID 9864266, compound

HRID 1596204Notes

Reaction equation

HRID 1596204 reaction equation
[H-].[Na+].[CH3:3][C:4]1[C:5]([CH2:10][OH:11])=[N:6][CH:7]=[CH:8][CH:9]=1.Cl[C:13]1[C:14]([CH:28]2[CH2:31][CH2:30][CH2:29]2)=[CH:15][C:16]2[N:17]([C:19]([C:22]3[CH:23]=[N:24][CH:25]=[CH:26][CH:27]=3)=[N:20][N:21]=2)[N:18]=1>CN(C=O)C.O>[CH:28]1([C:14]2[C:13]([O:11][CH2:10][C:5]3[C:4]([CH3:3])=[CH:9][CH:8]=[CH:7][N:6]=3)=[N:18][N:17]3[C:19]([C:22]4[CH:23]=[N:24][CH:25]=[CH:26][CH:27]=4)=[N:20][N:21]=[C:16]3[CH:15]=2)[CH2:29][CH2:30][CH2:31]1

Participants

6

Reactant 3

HCID 24758Sodium hydrideHCID 1514369(3-Methylpyridin-2-yl)methanolHCID 21701622HCID 21701622, compound

Product 1

HCID 9864266HCID 9864266, compoundYield 14.5%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

Sodium hydride (60% dispersion in oil, 13.4 mg, 0.34 mmol) was added to a solution of (3-methylpyridin-2-yl)methanol (38 mg, 0.31 mmol) in dry DMF (1 ml) at room temperature. After 1 h at room temperature a solution of 6-chloro-7-cyclobutyl-3-(pyridin-3-yl)-1,2,4-triazolo[4,3-b]pyridazine (80 mg, 0.28 mmol) was added and the reaction stirred for 18 h. The reaction mixture was diluted with water (10 ml) and stirred for 10 minutes after which time the mixture was filtered and the residue washed, first with water, then with diethyl ether. The residue was purified by chromatography on silica gel, eluting with 0-5% dichloromethane-methanol to afford the title pyridazine (15.1 mg, 14%). 1NMR (250 MHz, CDCl3) δ1.83-1.89 (1H, m), 1.96-2.23 (3H, m), 2.28-2.40 (2H, m), 2.43 (3H, s), 3.57-3.67 (1H, m), 5.59 (2H, s), 7.23 (1H, m), 7.45-7.50 (1H, m), 7.58-7.61 (1H, d, J=7.6 Hz), 7.85 (1H, d, J=1.5 Hz), 8.49 (1H, m), 8.66 (2H, m), 9.71 (1H, br s). MS (ES+) m/e 373 [MH]+.

Workup

  1. stirringstirred for 10 minutes after which time the mixture
  2. filtrationwas filtered
  3. washthe residue washed, first with water
  4. customThe residue was purified by chromatography on silica gel
  5. washeluting with 0-5% dichloromethane-methanol

Sources & evidence

ORD record
ord-83e436a87a7a4eb594e7e72f223d31ca
Source dataset
uspto-grants-2001_09
Patent number
US06291460B1

Reaction notes

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