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

HRID 1399684Notes

Reaction equation

[OH-].[Na+].ClC1C=CC([C:10]2[C:15]([CH:16]([CH2:21][CH2:22][CH3:23])[C:17]([O:19]C)=[O:18])=[C:14]([CH3:24])[N:13]=[C:12]([C:25]3[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=3)[N:11]=2)=C(OC)C=1>CO>[CH2:12]([C:10]1[C:15]([CH:16]([CH2:21][CH2:22][CH3:23])[C:17]([OH:19])=[O:18])=[C:14]([CH3:24])[N:13]=[C:12]([C:25]2[CH:26]=[CH:27][CH:28]=[CH:29][CH:30]=2)[N:11]=1)[C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1

Participants

Conditions

Temperature: 60 °C

Procedure

A solution of sodium hydroxide 10N (0.300 mL; 3.0 mmol) was added to a mixture of methyl 2-(4-(4-chloro-2-methoxyphenyl)-6-methyl-2-phenylpyrimidin-5-yl)pentanoate (0.095 g; 0.254 mmol) in methanol (3 mL). The mixture was heated at 60° C. in a sealed tube for 18 h and then concentrated under reduced pressure. The residue was dissolved in water and the pH of the solution was adjusted between 2 and 3 by addition of a solution of hydrochloric acid 6N until a precipitate formed. The precipitate was collected by filtration and dried under reduced pressure over phosphorus pentoxide to afford 0.078 g (84%) of the title compound as a yellow solid.

Workup

concentrationconcentrated under reduced pressure
dissolutionThe residue was dissolved in water
additionthe pH of the solution was adjusted between 2 and 3 by addition of a solution of hydrochloric acid 6N until a precipitate
customformed
filtrationThe precipitate was collected by filtration
dry with materialdried under reduced pressure over phosphorus pentoxide

Sources & evidence

ORD record: ord-796dadd078c9483c93624e5110cf532c
Source dataset: uspto-grants-2014_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08906906B2

Reaction notes

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