Diisopropylamine → HCID 22145904, compound

HRID 1825415Notes

Reaction equation

[CH2:1]([Li])[CH2:2][CH2:3][CH3:4].C(NC(C)C)(C)C.Cl[C:14]1[CH:15]=[N:16][CH:17]=C(Cl)[C:19]=1C.[CH3:22][O:23][C:24]1[CH:25]=[C:26]([CH:32]=[O:33])[N:27]=[N:28][C:29]=1[O:30][CH3:31]>CCCCCC.O1CCCC1>[CH3:4][C:3]1[CH:17]=[N:16][CH:15]=[C:14]([CH3:19])[C:2]=1[CH2:1][CH:32]([C:26]1[N:27]=[N:28][C:29]([O:30][CH3:31])=[C:24]([O:23][CH3:22])[CH:25]=1)[OH:33]

Participants

Conditions

Temperature: -70 °C

Procedure

n-Butyllithium (1.51 mL of a 1.6 M solution in hexane) is added to a solution of diisopropylamine (0.34 mL) in tetrahydrofuran (29 mL) at −10° C. under a nitrogen atmosphere. After 30 minutes the mixture is cooled to −70° C. and a solution of 3,5-dichloro-4-methylpyridine (0.39 g) in tetrahydrofuran (4 mL) is added dropwise. After 30 minutes a solution of 5,6-dimethoxy-pyridazine-3-carboxaldehyde (0.35 g) in tetrahydrofuran (15 mL) is added at −70 to −60° C. and stirring continued at this temperature for 1 hour before cooling is discontinued. After 24 hours the yellow solution is quenched by the addition of aqueous ammonium chloride and the mixture extracted with ethyl acetate. The dried extracts (MgSO4) are evaporated and the residue purified by flash chromatography (ethyl acetate as eluent on silica) to give (±)-2-(3,5-dimethylpyrid-4-yl)-1-(5,6-dimethoxypyridazin-3-yl)ethanol (0.17 g), as a white solid, m.p. 217–8° C.

Workup

temperaturebefore cooling
customAfter 24 hours the yellow solution is quenched by the addition of aqueous ammonium chloride
extractionthe mixture extracted with ethyl acetate
customThe dried extracts (MgSO4) are evaporated
customthe residue purified by flash chromatography (ethyl acetate as eluent on silica)

Sources & evidence

ORD record: ord-b3c43a60a0794cff8730752580248d6a
Source dataset: uspto-grants-2006_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07045660B2

Reaction notes

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