Sodium Hydroxide → 2-(4-Methyl-2-(piperidin-1-yl)-6-p-tolylpyrimidin-5-yl)pentanoic acid

HRID 1399590Notes

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][C:19]([CH3:22])=[CH:18][CH:17]=2)[N:5]=[C:4]([N:23]2[CH2:28][CH2:27][CH2:26][CH2:25][CH2:24]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:17]=[CH:18][C:19]([CH3:22])=[CH:20][CH:21]=2)[N:5]=[C:4]([N:23]2[CH2:24][CH2:25][CH2:26][CH2:27][CH2:28]2)[N:3]=1

Participants

Conditions

Temperature: 100 °C

Procedure

To a solution of methyl 2-(4-methyl-2-(piperidin-1-yl)-6-p-tolylpyrimidin-5-yl)pentanoate (63 mg; 0.16 mmol) in methanol (1.651 mL) was added a 10 N sodium hydroxide solution (165 μL; 1.651 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 47.6 mg (77%) of the title compound as a white solid. ESI/APCI(+): 368 (M+H). ESI/APCI(−): 366. 1H NMR (DMSO-d6) δ 7.29 (4H, m); 3.71 (4H, m); 3.68 (1H, m); 2.35 (3H, s); 2.28 (3H, s); 1.89 (1H, m); 1.60 (2H, m); 1.50 (4H, m); 1.44 (1H, m); 0.89 (2H, m); 0.59 (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-99843d9526ad49118606174df10f8fde
Source dataset: uspto-grants-2014_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08906906B2

Reaction notes

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