Diisopropylamine → HCID 22145904, compound

HRID 993306Notes

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-d27e531ea5804fa297e1abced04860b2
Source dataset: uspto-grants-2002_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06472412B1

Reaction notes

Loading…