Sodium Hydroxide → HCID 50997700, compound

HRID 1399570Notes

Reaction equation

HRID 1399570 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](/[CH:22]=[CH: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](/[CH:22]=[CH: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 50996264HCID 50996264, compound

Product 1

HCID 50997700HCID 50997700, compoundYield 41.2%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

A solution of (E)-methyl 2-(4-methyl-6-phenyl-2-styrylpyrimidin-5-yl)pentanoate (73 mg; 0.189 mmol) in ethanol (1 mL), tetrahydrofuran (1 mL) and 2N sodium hydroxide solution (0.944 mL; 1.889 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 solution. The formed 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 29 mg (40%) of the title compound as a colorless oil. ESI/APCI(+): 373 (M+H).

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. additiondiluted with water
  3. extractionThe formed 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-b02e296f9e044db0b13796992435691f
Source dataset
uspto-grants-2014_12
Patent number
US08906906B2

Reaction notes

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