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

HRID 1399585Notes

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]([C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)[N:3]=1.[OH-].[Na+]>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][C:19]([CH3:22])=[CH:20][CH:21]=2)[N:5]=[C:4]([C:23]2[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=2)[N:3]=1

Participants

Conditions

Temperature: 100 °C

Procedure

To a solution of methyl 2-(4-methyl-2-phenyl-6-p-tolylpyrimidin-5-yl)pentanoate (80 mg; 0.214 mmol) in tetrahydrofuran (2.136 mL) was added a 10 N sodium hydroxide solution (214 μL; 2.136 mmol) and the mixture was heated at 100° C. for 18 h. The volatiles were removed under reduced pressure and the mixture was acidified by adding 6N hydrochloric acid. The suspension was extracted twice with ethyl acetate. The combined organic layers were washed with a saturated sodium chloride solution, dried over magnesium sulphate and concentrated under reduced pressure to give 31 mg (40%) of the title compound as a white solid. ESI/APCI(+): 361 (M+H).

Workup

customThe volatiles were removed under reduced pressure
additionby adding 6N hydrochloric acid
extractionThe suspension was extracted twice with ethyl acetate
washThe combined organic layers were washed with a saturated sodium chloride solution
dry with materialdried over magnesium sulphate
concentrationconcentrated under reduced pressure

Sources & evidence

ORD record: ord-47fc2dc2311c4d218d3079fd49f6078c
Source dataset: uspto-grants-2014_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08906906B2

Reaction notes

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