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

HRID 2284797Notes

Reaction equation

HRID 2284797 reaction equation
[Si]([O:8][CH2:9][CH2:10][C:11]1[CH:15]=[C:14]([C:16]2[C:17]([NH:30][CH2:31][CH2:32][CH3:33])=[N:18][C:19]([NH:22][C:23]3[CH:28]=[CH:27][CH:26]=[C:25]([F:29])[CH:24]=3)=[N:20][CH:21]=2)[O:13][N:12]=1)(C(C)(C)C)(C)C.[F-].C([N+](CCCC)(CCCC)CCCC)CCC.C(=O)([O-])O.[Na+].C(OCC)(=O)C>O1CCCC1>[F:29][C:25]1[CH:24]=[C:23]([NH:22][C:19]2[N:18]=[C:17]([NH:30][CH2:31][CH2:32][CH3:33])[C:16]([C:14]3[O:13][N:12]=[C:11]([CH2:10][CH2:9][OH:8])[CH:15]=3)=[CH:21][N:20]=2)[CH:28]=[CH:27][CH:26]=1

Participants

6

Reactant 4

HCID 8857Ethyl AcetateHCID 516892Sodium BicarbonateHCID 2724141Tetrabutylammonium FluorideHCID 1317335355-(3-(2-((tert-butyldimethylsilyl)oxy)ethyl)isoxazol-5-yl)-N2-(3-fluorophenyl)-N4-propylpyrimidine-2,4-diamine

Product 1

HCID 900517642-(5-(2-((3-Fluorophenyl)amino)-4-(propylamino)pyrimidin-5-yl)isoxazol-3-yl)ethanol

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of 5-(3-(2-((tert-butyldimethylsilyl)oxy)ethyl)isoxazol-5-yl)-N2-(3-fluorophenyl)-N4-propylpyrimidine-2,4-diamine (S4, 22 mg) in tetrahydrofuran (1 mL), a 1.0 mol/L solution of tetrabutylammonium fluoride in tetrahydrofuran (69 μL) was added under ice cooling, and the mixture was stirred at room temperature for 3 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 magnesium sulfate, and the solvent was evaporated under reduced pressure. The obtained residue was purified by silica gel column chromatography (eluent, 70 to 5% hexane in ethyl acetate) to obtain 2-(5-(2-((3-fluorophenyl)amino)-4-(propylamino)pyrimidin-5-yl)isoxazol-3-yl)ethanol (S5, 5.3 mg) as white solid.

Workup

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

Sources & evidence

ORD record
ord-31ac2e4c76614e919640327a2db52666
Source dataset
uspto-grants-2015_09
Patent number
US09145415B2

Reaction notes

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