Tetrahydrofuran → HCID 11236657, compound

HRID 2422170Notes

Reaction equation

HRID 2422170 reaction equation
C1COCC1.[Cl:6][C:7]1[C:12]([CH2:13][C:14]([O:16]C)=[O:15])=[C:11]([Cl:18])[N:10]=[C:9]([CH2:19][C:20]2[CH:25]=[CH:24][C:23]([NH:26][C:27]([C:29]3[CH:38]=[CH:37][C:36]4[C:31](=[CH:32][CH:33]=[CH:34][CH:35]=4)[CH:30]=3)=[O:28])=[CH:22][CH:21]=2)[N:8]=1.[OH-].[Na+]>O>[Cl:18][C:11]1[C:12]([CH2:13][C:14]([OH:16])=[O:15])=[C:7]([Cl:6])[N:8]=[C:9]([CH2:19][C:20]2[CH:21]=[CH:22][C:23]([NH:26][C:27]([C:29]3[CH:38]=[CH:37][C:36]4[C:31](=[CH:32][CH:33]=[CH:34][CH:35]=4)[CH:30]=3)=[O:28])=[CH:24][CH:25]=2)[N:10]=1

Participants

5

Reactant 3

HCID 8028TetrahydrofuranHCID 14798Sodium HydroxideHCID 59514514HCID 59514514, compound

Product 1

HCID 11236657HCID 11236657, compoundYield 15%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A THF (1.5 mL) solution of methyl {4,6-dichloro-2-[4-(2-naphthoylamino)benzyl]pyrimidin-5-yl}acetate (0.048 g, 0.10 mmol) at room temperature was treated with 1N NaOH (1 mL). After stirring for 16 hours at room temperature, the reaction mixture was poured into water and washed with EtOAc. The aqueous layer was acidified with 1N HCl and back extracted with EtOAc. The combined organic extracts was washed with brine, dried over anhydrous MgSO4, filtered, and concentrated in vacuo. The remaining residue was chromatographed over silica gel eluting with 10% THF in CH2Cl2 containing 0.5% AcOH to give {4,6-dichloro-2-[4-(2-naphthoyl-amino)benzyl]pyrimidin-5-yl}acetic acid (0.007 g, 15% yield) as a white solid.

Workup

  1. washwashed with EtOAc
  2. extractionback extracted with EtOAc
  3. washThe combined organic extracts was washed with brine
  4. dry with materialdried over anhydrous MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customThe remaining residue was chromatographed over silica gel eluting with 10% THF in CH2Cl2 containing 0.5% AcOH

Sources & evidence

ORD record
ord-4c0a365b297b42d9838dab89d18540a0
Source dataset
uspto-grants-2011_06
Patent number
US07960393B2

Reaction notes

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