Potassium sodium tartarate → HCID 69311595, compound

HRID 860501Notes

Reaction equation

[H-].[H-].[H-].[H-].[Li+].[Al+3].C([O:9][C:10](=O)[CH2:11][C:12]1[C:17]([CH3:18])=[N:16][N:15]2[C:19]([CH2:22][CH3:23])=[CH:20][CH:21]=[C:14]2[C:13]=1[C:24]1[CH:25]=[N:26][CH:27]=[C:28]([Br:30])[CH:29]=1)C.C(C(C(C([O-])=O)O)O)([O-])=O.[Na+].[K+]>C1COCC1>[Br:30][C:28]1[CH:29]=[C:24]([C:13]2[C:14]3[N:15]([C:19]([CH2:22][CH3:23])=[CH:20][CH:21]=3)[N:16]=[C:17]([CH3:18])[C:12]=2[CH2:11][CH2:10][OH:9])[CH:25]=[N:26][CH:27]=1

Participants

Conditions

Temperature: 0 °C

Procedure

To a suspension of LiAlH4 (113 mg) in THF (10 mL) was added ethyl[4-(5-bromo-3-pyridinyl)-7-ethyl-2-methylpyrrolo[1,2-b]pyridazin-3-yl]acetate (600 mg) under ice-water cooling and the mixture was stirred at 0° C. for 2 hours. To the mixture was added potassium sodium tartrate solution and the insolubles were filterred off. After evaporation of solvent, the residue was partitioned between AcOEt and water. The organic layer was separated, washed with brine, dried over MgSO4, and evaporated in vacuo. The residue was purified by silica gel column chromatography eluting with a mixture of hexane and AcOEt (5:1-1:1) to give 2-[4-(5-bromo-3-pyridinyl)-7-ethyl-2-methylpyrrolo[1,2-b]pyridazin-3-yl]ethanol as yellow oil (246 mg).

Workup

customAfter evaporation of solvent
customthe residue was partitioned between AcOEt and water
customThe organic layer was separated
washwashed with brine
dry with materialdried over MgSO4
customevaporated in vacuo
customThe residue was purified by silica gel column chromatography
washeluting with a mixture of hexane and AcOEt (5:1-1:1)

Sources & evidence

ORD record: ord-5323b8ef11574c809c80b60a66297e43
Source dataset: uspto-grants-2006_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07153854B2

Reaction notes

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