Lithium Hydroxide → HCID 22063567, compound

HRID 1828522Notes

Reaction equation

HRID 1828522 reaction equation
[CH:1]([C:4]1[N:5]=[C:6]([CH2:9][CH2:10][C:11]2[CH:35]=[CH:34][N:14]3[C:15](=[O:33])[C:16](/[CH:25]=[C:26](\[CH3:32])/[C:27]([O:29]CC)=[O:28])=[C:17]([N:19]4[CH2:24][CH2:23][O:22][CH2:21][CH2:20]4)[N:18]=[C:13]3[CH:12]=2)[S:7][CH:8]=1)([CH3:3])[CH3:2].[OH-].[Li+]>O1CCCC1.CO.O>[CH:1]([C:4]1[N:5]=[C:6]([CH2:9][CH2:10][C:11]2[CH:35]=[CH:34][N:14]3[C:15](=[O:33])[C:16](/[CH:25]=[C:26](\[CH3:32])/[C:27]([OH:29])=[O:28])=[C:17]([N:19]4[CH2:24][CH2:23][O:22][CH2:21][CH2:20]4)[N:18]=[C:13]3[CH:12]=2)[S:7][CH:8]=1)([CH3:3])[CH3:2]

Participants

6

Reactant 2

HCID 3939Lithium HydroxideHCID 86588145HCID 86588145, compound2×

Product 1

HCID 22063567HCID 22063567, compoundYield 33.3%

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 962WaterSolvent2×HCID 8028TetrahydrofuranSolvent

Procedure

The ethyl (E)-3-{8-[2-(4-isopropyl-1,3-thiazol-2-yl)ethyl]-2-morpholino-4-oxo-4H-pyrido[1,2-a]pyrimidin-3-yl}-2-methyl-2-propenoate (14 mg) obtained in (A) was dissolved in tetrahydrofuran (4 ml) and methanol (1 ml), added with a solution of lithium hydroxide (1.4 mg) in water (1 ml) and stirred at room temperature for 1.5 hours. The reaction mixture was added with water and washed with ether, and then the aqueous layer was made acidic with diluted hydrochloric acid and extracted with ethyl acetate. The organic layer was dried over magnesium sulfate, and the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography to obtain the title compound (4.4 mg) as yellow powder.

Workup

  1. washwashed with ether
  2. extractionextracted with ethyl acetate
  3. dry with materialThe organic layer was dried over magnesium sulfate
  4. customthe solvent was evaporated under reduced pressure
  5. customThe residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-d32fab37da304bda851564fa30b7f933
Source dataset
uspto-grants-2006_06
Patent number
US07056917B2

Reaction notes

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