Ethyl Acetate → (2-((3-Fluorophenyl)amino)-4-(propylamino)pyrimidin-5-yl)methanol

HRID 2284701Notes

Reaction equation

HRID 2284701 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].[F:7][C:8]1[CH:9]=[C:10]([NH:14][C:15]2[N:20]=[C:19]([NH:21][CH2:22][CH2:23][CH3:24])[C:18]([C:25](OCC)=[O:26])=[CH:17][N:16]=2)[CH:11]=[CH:12][CH:13]=1.C(OCC)(=O)C>O1CCCC1>[F:7][C:8]1[CH:9]=[C:10]([NH:14][C:15]2[N:20]=[C:19]([NH:21][CH2:22][CH2:23][CH3:24])[C:18]([CH2:25][OH:26])=[CH:17][N:16]=2)[CH:11]=[CH:12][CH:13]=1

Participants

5

Reactant 3

HCID 8857Ethyl AcetateHCID 21226445Aluminium lithium hydride2×HCID 90052261HCID 90052261, compound

Product 1

HCID 90052116(2-((3-Fluorophenyl)amino)-4-(propylamino)pyrimidin-5-yl)methanolYield 54.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a suspension of lithium aluminum hydride (160 mg) in tetrahydrofuran (14 mL), ethyl 2-((3-fluorophenyl)amino)-4-(propylamino)pyrimidine-5-carboxylate (E3, 450 mg) was added under ice cooling, and the mixture was stirred at the same temperature for 1 hour and 30 minutes. To the reaction mixture, lithium aluminum hydride (80 mg) was added under ice cooling, and the mixture was stirred at the same temperature for 1 hour. To the reaction mixture, ethyl acetate and an aqueous solution of the Rochell salt were added at room temperature, and the mixture was stirred at the same temperature for 2 hours and 30 minutes. The insoluble matter was removed by filtration through Cerite. The organic layer was separated, washed with 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, 100 to 90% ethyl acetate in methanol) to obtain (2-((3-fluorophenyl)amino)-4-(propylamino)pyrimidin-5-yl)methanol (E13, 212 mg).

Workup

  1. additionwas added under ice cooling
  2. stirringthe mixture was stirred at the same temperature for 1 hour
  3. stirringthe mixture was stirred at the same temperature for 2 hours and 30 minutes
  4. customThe insoluble matter was removed by filtration through Cerite
  5. customThe organic layer was separated
  6. washwashed with saturated aqueous sodium chloride
  7. dry with materialdried over anhydrous sodium sulfate
  8. customthe solvent was evaporated under reduced pressure
  9. customThe obtained residue was purified by silica gel column chromatography (eluent, 100 to 90% ethyl acetate in methanol)

Sources & evidence

ORD record
ord-05680d20488d448a84753ae52b34a792
Source dataset
uspto-grants-2015_09
Patent number
US09145415B2

Reaction notes

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