Sodium Hydroxide → HCID 50994997, compound

HRID 1399623Notes

Reaction equation

[OH-].[Na+].[CH2:3]([N:5]1[CH2:11][CH2:10][CH2:9][N:8]([C:12]2[N:17]=[C:16]([CH3:18])[C:15]([CH:19]([CH2:24][CH2:25][CH3:26])[C:20]([O:22]C)=[O:21])=[C:14]([C:27]3[CH:32]=[CH:31][C:30]([CH3:33])=[CH:29][CH:28]=3)[N:13]=2)[CH2:7][CH2:6]1)[CH3:4]>CO>[CH2:3]([N:5]1[CH2:11][CH2:10][CH2:9][N:8]([C:12]2[N:17]=[C:16]([CH3:18])[C:15]([CH:19]([CH2:24][CH2:25][CH3:26])[C:20]([OH:22])=[O:21])=[C:14]([C:27]3[CH:28]=[CH:29][C:30]([CH3:33])=[CH:31][CH:32]=3)[N:13]=2)[CH2:7][CH2:6]1)[CH3:4]

Participants

Conditions

Temperature: 100 °C

Procedure

A solution of sodium hydroxide 5N (0.5 mL) was added to a mixture of methyl 2-(2-(4-ethyl-1,4-diazepan-1-yl)-4-methyl-6-p-tolylpyrimidin-5-yl)pentanoate (0.030 g; 0.070 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. The crude mixture was purified by preparative HPLC (HPLC method 5) furnished 0.016 g (60%) 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
customThe crude mixture was purified by preparative HPLC (HPLC method 5)

Sources & evidence

ORD record: ord-54665081d8ef46258383ff75b1311abe
Source dataset: uspto-grants-2014_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08906906B2

Reaction notes

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