Tetrahydrofuran → HCID 90051712, compound

HRID 2284800Notes

Reaction equation

HRID 2284800 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[C:7](Cl)=[N:8][C:9]([S:12][CH3:13])=[N:10][CH:11]=1)=[O:5])[CH3:2].[C:15](=[O:18])([O-])O.[Na+].C(O[CH2:24][CH3:25])(=O)C.O1[CH2:30][CH2:29][CH2:28][CH2:27]1>CN(C)C=O.C(O)C1C=CC=CC=1.[H-].[Na+]>[CH2:15]([O:18][C:7]1[C:6]([C:4]([O:3][CH2:1][CH3:2])=[O:5])=[CH:11][N:10]=[C:9]([S:12][CH3:13])[N:8]=1)[C:25]1[CH:24]=[CH:30][CH:29]=[CH:28][CH:27]=1

Participants

8

Reactant 4

HCID 8028TetrahydrofuranHCID 8857Ethyl AcetateHCID 800084-Chloro-2-(methylthio)pyrimidine-5-carboxylic acid ethyl esterHCID 516892Sodium Bicarbonate

Product 1

HCID 90051712HCID 90051712, compound

Reagents, catalysts & solvents 3

HCID 244Benzyl AlcoholSolventHCID 6228DimethylformamideSolventHCID 24758Sodium hydrideSolvent

Procedure

To a solution of 4-chloro-2-(methylthio)pyrimidine-5-carboxylic acid ethyl ester (5.0 g) in tetrahydrofuran (50 mL) and N,N-dimethylformamide (5 mL), benzyl alcohol (2.66 mL) and sodium hydride (60% wt, 946 mg) were added under ice cooling, and the mixture was stirred at the same temperature for 2 hours. To the reaction mixture, saturated aqueous sodium hydrogencarbonate and ethyl acetate were added. 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 to obtain oily ethyl 4-(benzyloxy)-2-(methylthio)pyrimidine-5-carboxylate (S25, 5.37 g).

Workup

  1. customThe organic layer was separated
  2. washwashed successively with water and saturated aqueous sodium chloride
  3. dry with materialdried over anhydrous sodium sulfate
  4. customthe solvent was evaporated under reduced pressure
  5. customThe obtained residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-53fe5993ad6443e5992f6b866a4488a6
Source dataset
uspto-grants-2015_09
Patent number
US09145415B2

Reaction notes

Loading…