Ethyl Acetate → HCID 90051713, compound

HRID 2284801Notes

Reaction equation

HRID 2284801 reaction equation
[CH2:1]([O:8][C:9]1[C:14]([C:15](OCC)=[O:16])=[CH:13][N:12]=[C:11]([S:20][CH3:21])[N:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[H-].[Al+3].[Li+].[H-].[H-].[H-].C(=O)([O-])O.[Na+].C(OCC)(=O)C>O1CCCC1>[CH2:1]([O:8][C:9]1[C:14]([CH2:15][OH:16])=[CH:13][N:12]=[C:11]([S:20][CH3:21])[N:10]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 4

HCID 8857Ethyl AcetateHCID 516892Sodium BicarbonateHCID 21226445Aluminium lithium hydrideHCID 90051712HCID 90051712, compound

Product 1

HCID 90051713HCID 90051713, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of ethyl 4-(benzyloxy)-2-(methylthio)pyrimidine-5-carboxylate (S25, 3.02 g) in tetrahydrofuran (50 mL), lithium aluminum hydride (1.51 g) was added portionwise under ice cooling, and the mixture was stirred at the same temperature for 45 minutes. To the reaction mixture, saturated aqueous sodium hydrogencarbonate (300 mL) and ethyl acetate (200 mL) were added. The insoluble matter was removed by filtration through Cerite. The organic layer was separated, washed successively with water and saturated aqueous sodium chloride, and then dried over anhydrous sodium sulfate, and the solvent was evaporated under reduced pressure. The obtained residue was purified by silica gel column chromatography (eluent, 70 to 30% hexane in ethyl acetate) to obtain oily (4-(benzyloxy)-2-(methylthio)pyrimidin-5-yl)methanol (S26, 818 mg).

Workup

  1. customThe insoluble matter was removed by filtration through Cerite
  2. customThe organic layer was separated
  3. washwashed successively with water and saturated aqueous sodium chloride
  4. dry with materialdried over anhydrous sodium sulfate
  5. customthe solvent was evaporated under reduced pressure
  6. customThe obtained residue was purified by silica gel column chromatography (eluent, 70 to 30% hexane in ethyl acetate)

Sources & evidence

ORD record
ord-b1abff407386445d861a58156b491110
Source dataset
uspto-grants-2015_09
Patent number
US09145415B2

Reaction notes

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