Sodium Hydroxide → HCID 50995372, compound

HRID 1399619Notes

Reaction equation

[OH-].[Na+].[CH3:3][N:4]([CH3:32])[C@@H:5]1[CH2:9][CH2:8][N:7]([C:10]2[N:15]=[C:14]([CH3:16])[C:13]([CH:17]([CH2:22][CH2:23][CH3:24])[C:18]([O:20]C)=[O:19])=[C:12]([C:25]3[CH:30]=[CH:29][C:28]([CH3:31])=[CH:27][CH:26]=3)[N:11]=2)[CH2:6]1>CO>[CH3:32][N:4]([CH3:3])[C@H:5]1[CH2:9][CH2:8][N:7]([C:10]2[N:15]=[C:14]([CH3:16])[C:13]([CH:17]([CH2:22][CH2:23][CH3:24])[C:18]([OH:20])=[O:19])=[C:12]([C:25]3[CH:26]=[CH:27][C:28]([CH3:31])=[CH:29][CH:30]=3)[N:11]=2)[CH2:6]1

Participants

Conditions

Temperature: 100 °C

Procedure

A solution of sodium hydroxide 5N (0.5 mL) was added to a mixture of methyl 2-(2-((R)-3-(dimethylamino)pyrrolidin-1-yl)-4-methyl-6-p-tolylpyrimidin-5-yl)pentanoate (0.053 g; 0.116 mmol) in methanol (1.5 mL). The mixture was heated in a sealed tube at 100° C. for 18 h and then concentrated under reduced pressure. The residue was dissolved in water and the pH of the solution was adjusted between 3 and 4 by addition of a solution of hydrochloric acid 6N. The aqueous layer was extracted with ethyl acetate and concentrated under reduced pressure. Purification by preparative HPLC (HPLC method 5) furnished 0.007 g (14%) of the title compound as a white solid.

Workup

concentrationconcentrated under reduced pressure
dissolutionThe residue was dissolved in water
additionthe pH of the solution was adjusted between 3 and 4 by addition of a solution of hydrochloric acid 6N
extractionThe aqueous layer was extracted with ethyl acetate
concentrationconcentrated under reduced pressure
customPurification by preparative HPLC (HPLC method 5)

Sources & evidence

ORD record: ord-86b615902c034fe89e81317eaf5b2b9b
Source dataset: uspto-grants-2014_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08906906B2

Reaction notes

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