Sodium Hydroxide → HCID 50995370, compound

HRID 1399614Notes

Reaction equation

[OH-].[Na+].[CH:3]([C:6]1[N:10]=[C:9]([CH:11]2[CH2:16][CH2:15][CH2:14][N:13]([C:17]3[N:22]=[C:21]([CH3:23])[C:20]([CH:24]([CH2:29][CH2:30][CH3:31])[C:25]([O:27]C)=[O:26])=[C:19]([C:32]4[CH:37]=[CH:36][C:35]([CH3:38])=[CH:34][CH:33]=4)[N:18]=3)[CH2:12]2)[O:8][N:7]=1)([CH3:5])[CH3:4]>CO>[CH:3]([C:6]1[N:10]=[C:9]([CH:11]2[CH2:16][CH2:15][CH2:14][N:13]([C:17]3[N:22]=[C:21]([CH3:23])[C:20]([CH:24]([CH2:29][CH2:30][CH3:31])[C:25]([OH:27])=[O:26])=[C:19]([C:32]4[CH:33]=[CH:34][C:35]([CH3:38])=[CH:36][CH:37]=4)[N:18]=3)[CH2:12]2)[O:8][N:7]=1)([CH3:5])[CH3:4]

Participants

Conditions

Temperature: 100 °C

Procedure

A solution of sodium hydroxide 5N (1 mL) was added to a mixture of methyl 2-(2-(3-(3-isopropyl-1,2,4-oxadiazol-5-yl)piperidin-1-yl)-4-methyl-6-p-tolylpyrimidin-5-yl)pentanoate (0.026 g; 0.053 mmol) in methanol (1 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 2 and 3 by addition of a solution of hydrochloric acid 6N. The precipitate was collected by filtration and dried under reduced pressure over phosphorus pentoxide to give 0.084 g (33%) 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 2 and 3 by addition of a solution of hydrochloric acid 6N
filtrationThe precipitate was collected by filtration
dry with materialdried under reduced pressure over phosphorus pentoxide

Sources & evidence

ORD record: ord-f2bed9460e7b48bfbca6ed144615e1a1
Source dataset: uspto-grants-2014_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08906906B2

Reaction notes

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