Sodium Hydroxide → HCID 50997511, compound

HRID 1399572Notes

Reaction equation

HRID 1399572 reaction equation
[CH3:1][C:2]1[C:7]([CH:8]([CH2:13][CH2:14][CH3:15])[C:9]([O:11]C)=[O:10])=[C:6]([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[N:5]=[C:4]([CH2:22][CH2:23][C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)[N:3]=1.[OH-].[Na+]>C(O)C.O1CCCC1>[CH3:1][C:2]1[C:7]([CH:8]([CH2:13][CH2:14][CH3:15])[C:9]([OH:11])=[O:10])=[C:6]([C:16]2[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=2)[N:5]=[C:4]([CH2:22][CH2:23][C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)[N:3]=1

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 50997510HCID 50997510, compound

Product 1

HCID 50997511HCID 50997511, compoundYield 27.3%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

A solution of methyl 2-(4-methyl-2-phenethyl-6-phenylpyrimidin-5-yl)pentanoate (91 mg; 0.235 mmol) in ethanol (1.5 mL), tetrahydrofuran (0.5 mL) and 2N sodium hydroxide solution (1.5 mL; 3.0 mmol) was stirred for 24 h at room temperature. The reaction mixture was concentrated under reduced pressure, diluted with water and acidified with a 6N hydrochloric acid. The suspension was extracted twice with ethyl acetate and the organic layers were washed with water and dried by filtration over a phase separater filter (PS1). The crude material was first purified by flash chromatography on silica gel using a linear gradient of methanol (1-10%) in dichloromethane and then by preparative thick layer chromatography on silica gel eluting with 10% methanol in dichloromethane to give 24 mg (26%) of the title compound as a colorless oil. ESI/APCI(+): 375 (M+H). ESI/APCI(−): 373 (M−H).

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. additiondiluted with water
  3. extractionThe suspension was extracted twice with ethyl acetate
  4. washthe organic layers were washed with water
  5. customdried by filtration over a phase separater
  6. filtrationfilter (PS1)
  7. customThe crude material was first purified by flash chromatography on silica gel using a linear gradient of methanol (1-10%) in dichloromethane

Sources & evidence

ORD record
ord-5506dcb6db734385b50e53717e48dab2
Source dataset
uspto-grants-2014_12
Patent number
US08906906B2

Reaction notes

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