Sodium Hydroxide → 2-(2-Benzyl-4-methyl-6-phenylpyrimidin-5-yl)pentanoic acid

HRID 1399569Notes

Reaction equation

HRID 1399569 reaction equation
[CH2:1]([C:8]1[N:13]=[C:12]([CH3:14])[C:11]([CH:15]([CH2:20][CH2:21][CH3:22])[C:16]([O:18]C)=[O:17])=[C:10]([C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)[N:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[OH-].[Na+]>C(O)C.O1CCCC1>[CH2:1]([C:8]1[N:13]=[C:12]([CH3:14])[C:11]([CH:15]([CH2:20][CH2:21][CH3:22])[C:16]([OH:18])=[O:17])=[C:10]([C:23]2[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=2)[N:9]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 50996263Methyl 2-(2-benzyl-4-methyl-6-phenylpyrimidin-5-yl)pentanoate

Product 1

HCID 509962652-(2-Benzyl-4-methyl-6-phenylpyrimidin-5-yl)pentanoic acidYield 40.8%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

A solution of methyl 2-(2-benzyl-4-methyl-6-phenylpyrimidin-5-yl)pentanoate (67 mg; 0.17 mmol) in ethanol (1 mL), tetrahydrofuran (1 mL) and 2N sodium hydroxide solution (0.895 mL; 1.789 mmol) was stirred for 40 h at room temperature. The reaction mixture was concentrated under reduced pressure, diluted with water and acidified with a 6N hydrochloric acid solution. 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 purified first 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 25 mg (37%) of the title compound as a colorless oil. ESI/APCI(+): 361 (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 purified first by flash chromatography on silica gel using a linear gradient of methanol (1-10%) in dichloromethane

Sources & evidence

ORD record
ord-fe2418df04654f94a8d95363fb8457c9
Source dataset
uspto-grants-2014_12
Patent number
US08906906B2

Reaction notes

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