Diisopropylamine → HCID 22145904, compound

HRID 1092853Notes

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-640a7c7bb37145f4ba3ead53c762555b
Source dataset: uspto-grants-2012_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08129537B2

Reaction notes

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