Sodium hydride → HCID 86662320, compound

HRID 449643Notes

Reaction equation

HRID 449643 reaction equation
[CH3:1][N:2]([CH3:8])[CH2:3][C:4]([CH3:7])([OH:6])[CH3:5].[Br:9][C:10]1[N:11]=[N:12][C:13](Br)=[CH:14][CH:15]=1.[H-].[Na+]>C1COCC1>[Br:9][C:10]1[N:11]=[N:12][C:13]([O:6][C:4]([CH3:7])([CH3:5])[CH2:3][N:2]([CH3:8])[CH3:1])=[CH:14][CH:15]=1

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 2488523,6-DibromopyridazineHCID 97937381-(Dimethylamino)-2-methylpropan-2-ol

Product 1

HCID 86662320HCID 86662320, compoundYield 65.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

In a 100 mL round bottom flask was added 1-(dimethylamino)-2-methylpropan-2-ol (1.48 g, 12.6 mmol, Eq: 1.5), THF and 3,6-dibromopyridazine (2 g, 8.41 mmol, Eq: 1.00). The flask was cooled to 0° C. followed by addition of NaH (572 mg, 14.3 mmol, Eq: 1.7) in one portion. The turbid reaction mixture was allowed to warm to room temperature and was stirred at room temperature overnight. The resultant black reaction mixture was absorbed onto silica gel and purified by LC chromatography eluting with 0-5% MeOH in 1/1 EtOAc/Hex to afford 1.5 g (65%) of the title compound.

Workup

  1. customThe turbid reaction mixture
  2. temperatureto warm to room temperature
  3. customThe resultant black reaction mixture
  4. customwas absorbed onto silica gel
  5. custompurified by LC chromatography
  6. washeluting with 0-5% MeOH in 1/1 EtOAc/Hex

Sources & evidence

ORD record
ord-40e996f4ac5b45199b6b38b6571d5db8
Source dataset
uspto-grants-2013_07
Patent number
US08481540B2

Reaction notes

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