Sodium Hydroxide → 2-[4-Methyl-6-phenyl-2-(1-piperidyl)pyrimidin-5-yl]pentanoic acid

HRID 1399576Notes

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]([N:22]2[CH2:27][CH2:26][CH2:25][CH2:24][CH2:23]2)[N:3]=1.[OH-].[Na+]>CO>[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:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[N:5]=[C:4]([N:22]2[CH2:27][CH2:26][CH2:25][CH2:24][CH2:23]2)[N:3]=1

Participants

Conditions

Temperature: 100 °C

Procedure

To a solution of methyl 2-(4-methyl-6-phenyl-2-(piperidin-1-yl)pyrimidin-5-yl)pentanoate (48 mg; 0.131 mmol) in methanol (1.306 mL) was added a 10 N sodium hydroxide solution (131 μL; 1.306 mmol) and the mixture was heated at 100° C. for 18 h. The volatiles were removed under reduced pressure and the residue was dissolved in water, the mixture was then acidified by adding 6N hydrochloric acid until a precipitate formed. The solid was isolated by filtration and dried under reduced pressure over phosphorus pentoxide to give 37 mg (80%) of the title compound as a white solid. ESI/APCI(+): 354 (M+H). 1H NMR (DMSO-d6) δ 12.58 (1H, br s); 7.44 (5H, m); 3.71 (4H, m); 3.63 (1H, m); 2.28 (3H, s); 1.88 (1H, m); 1.60 (2H, m); 1.50 (4H, m); 1.43 (1H, m); 0.90 (2H, m); 0.57 (3H, t).

Workup

customThe volatiles were removed under reduced pressure
dissolutionthe residue was dissolved in water
additionby adding 6N hydrochloric acid until a precipitate
customformed
customThe solid was isolated by filtration
dry with materialdried under reduced pressure over phosphorus pentoxide

Sources & evidence

ORD record: ord-7a10f16fccb343669a4109b4974da85d
Source dataset: uspto-grants-2014_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08906906B2

Reaction notes

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