Sodium Hydroxide → HCID 66955947, compound

HRID 1399625Notes

Reaction equation

[OH-].[Na+].[N:3]1([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)[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[CH2:5][CH2:4]1>CO>[N:3]1([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)[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[CH2:5][CH2:4]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-(indolin-1-yl)-4-methyl-6-p-tolylpyrimidin-5-yl)pentanoate (0.040 g; 0.096 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 precipitate was collected by filtration, dried under reduced pressure over phosphorous pentoxide and purified by preparative HPLC (HPLC method 5) furnished 0.010 g (25%) 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
filtrationThe precipitate was collected by filtration
dry with materialdried under reduced pressure over phosphorous pentoxide
custompurified by preparative HPLC (HPLC method 5)

Sources & evidence

ORD record: ord-28783bb8059e4225afd3f3d3f81971c8
Source dataset: uspto-grants-2014_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08906906B2

Reaction notes

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