Sodium Hydroxide → HCID 50997509, compound

HRID 1399610Notes

Reaction equation

HRID 1399610 reaction equation
[OH-].[Na+].[CH2:3]1[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[CH2:6][CH2:5][N:4]1[C:13]1[N:18]=[C:17]([CH3:19])[C:16]([CH:20]([CH2:25][CH2:26][CH3:27])[C:21]([O:23]C)=[O:22])=[C:15]([C:28]2[CH:33]=[CH:32][C:31]([CH3:34])=[CH:30][CH:29]=2)[N:14]=1>CO>[CH2:3]1[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[CH2:6][CH2:5][N:4]1[C:13]1[N:18]=[C:17]([CH3:19])[C:16]([CH:20]([CH2:25][CH2:26][CH3:27])[C:21]([OH:23])=[O:22])=[C:15]([C:28]2[CH:29]=[CH:30][C:31]([CH3:34])=[CH:32][CH:33]=2)[N:14]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 50996795HCID 50996795, compound

Product 1

HCID 50997509HCID 50997509, compoundYield 72%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
100 °C

Procedure

A solution of sodium hydroxide 5N (1 mL) was added to a mixture of methyl 2-(2-(3,4-dihydroisoquinolin-2(1H)-yl)-4-methyl-6-p-tolylpyrimidin-5-yl)pentanoate (0.072 g; 0.168 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 0.050 g (72%) of the title compound as a yellow solid.

Workup

  1. concentrationconcentrated under reduced pressure
  2. dissolutionThe residue was dissolved in water
  3. additionthe pH of the solution was adjusted between 2 and 3 by addition of a solution of hydrochloric acid 6N
  4. filtrationThe precipitate was collected by filtration
  5. dry with materialdried under reduced pressure over phosphorus pentoxide

Sources & evidence

ORD record
ord-79f42213e15041fd8f7e554ccd4179f7
Source dataset
uspto-grants-2014_12
Patent number
US08906906B2

Reaction notes

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