Water → HCID 117759967, compound

HRID 709818Notes

Reaction equation

HRID 709818 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].[F:7][C:8]1[CH:13]=[CH:12][C:11]([O:14][CH3:15])=[CH:10][C:9]=1[C:16]1[C:17]([O:27][CH2:28][CH:29]([CH3:31])[CH3:30])=[N:18][C:19]([C:22](OCC)=[O:23])=[N:20][CH:21]=1.O.[OH-].[Na+]>C(OCC)C>[F:7][C:8]1[CH:13]=[CH:12][C:11]([O:14][CH3:15])=[CH:10][C:9]=1[C:16]1[C:17]([O:27][CH2:28][CH:29]([CH3:31])[CH3:30])=[N:18][C:19]([CH2:22][OH:23])=[N:20][CH:21]=1

Participants

6

Reactant 4

HCID 962WaterHCID 14798Sodium HydroxideHCID 21226445Aluminium lithium hydrideHCID 117759857HCID 117759857, compound

Product 1

HCID 117759967HCID 117759967, compoundYield 44.4%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

To a suspension of lithium aluminum hydride (93 mg) in diethyl ether (5.0 mL) was added a solution of ethyl 5-(2-fluoro-5-methoxyphenyl)-4-isobutoxypyrimidine-2-carboxylate (284 mg) in diethyl ether (2.0 mL) at 0° C., and the mixture was stirred for 10 min. To the reaction mixture were added water and aqueous sodium hydroxide solution, and the resulting white precipitate was filtered off. The solvent in the filtrate was evaporated under reduced pressure, and the residue was dissolved in toluene (2.0 mL) and THF (1.0 mL). To the obtained solution was added 2,3-dichloro-5,6-dicyano-p-benzoquinone (277 mg), and the mixture was stirred at room temperature for 20 min. The solvent in the reaction mixture was evaporated under reduced pressure, and the residue was purified by silica gel column chromatography (NH, ethyl acetate/hexane) to give the title compound (111 mg) as a colorless solid.

Workup

  1. filtrationthe resulting white precipitate was filtered off
  2. customThe solvent in the filtrate was evaporated under reduced pressure
  3. dissolutionthe residue was dissolved in toluene (2.0 mL)
  4. additionTo the obtained solution was added 2,3-dichloro-5,6-dicyano-p-benzoquinone (277 mg)
  5. stirringthe mixture was stirred at room temperature for 20 min
  6. customThe solvent in the reaction mixture was evaporated under reduced pressure
  7. customthe residue was purified by silica gel column chromatography (NH, ethyl acetate/hexane)

Sources & evidence

ORD record
ord-0b42a5f7281b4ad2b8b77295c0eda731
Source dataset
uspto-grants-2015_11
Patent number
US09181186B2

Reaction notes

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