Sodium Hydroxide → 2-(4-Methyl-2,6-diphenylpyrimidin-5-yl)pentanoic acid

HRID 1399579Notes

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]([C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)[N:3]=1.[OH-].[Na+]>O1CCOCC1>[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]([C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)[N:3]=1

Participants

Conditions

Temperature: 100 °C

Procedure

To a solution of methyl 2-(4-methyl-2,6-diphenylpyrimidin-5-yl)pentanoate (80 mg; 0.222 mmol) in dioxane (1.5 mL) was added a 10 N sodium hydroxide solution (222 μL; 2.219 mmol) and the mixture was heated at 100° C. for 48 h. After removing the solvent under reduced pressure, the residue was dissolved in water, and acidified with a 6N hydrochloric acid. The precipitate was filtered, washed with water and dried under reduced pressure over phosphorus pentoxide to give 62 mg (80%) of the title compound as a white solid. ESI/APCI(+): 347 (M+H). ESI/APCI(−): 713 (2M−H+Na); 301 (M−CO2H).

Workup

customAfter removing the solvent under reduced pressure
dissolutionthe residue was dissolved in water
filtrationThe precipitate was filtered
washwashed with water
dry with materialdried under reduced pressure over phosphorus pentoxide

Sources & evidence

ORD record: ord-32d28069e148403f858ba003fe125dc5
Source dataset: uspto-grants-2014_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08906906B2

Reaction notes

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