Hydrochloric Acid → HCID 57329112, compound

HRID 81819Notes

Reaction equation

HRID 81819 reaction equation
[NH2:1][C:2]1[C:7]([O:8][C:9]2[C:10]([CH:19]([CH3:21])[CH3:20])=[CH:11][C:12]([O:17][CH3:18])=[C:13]([CH:16]=2)[C:14]#[N:15])=[CH:6][N:5]=[C:4]([NH:22][CH2:23][CH3:24])[N:3]=1.[OH-:25].[Na+].Cl>CCO.O.O>[NH2:1][C:2]1[C:7]([O:8][C:9]2[C:10]([CH:19]([CH3:20])[CH3:21])=[CH:11][C:12]([O:17][CH3:18])=[C:13]([CH:16]=2)[C:14]([NH2:15])=[O:25])=[CH:6][N:5]=[C:4]([NH:22][CH2:23][CH3:24])[N:3]=1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 595985715-(4-Amino-2-ethylamino-pyrimidin-5-yloxy)-4-isopropyl-2-methoxy-benzonitrile

Product 1

HCID 57329112HCID 57329112, compoundYield 27.1%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 19096565Water ethanolSolvent

Conditions

Temperature
100 °C

Procedure

To a solution of 5-(4-Amino-2-ethylamino-pyrimidin-5-yloxy)-4-isopropyl-2-methoxy-benzonitrile (0.3 g, 0.92 mmol) in EtOH/H2O (1:1, 10 ml) was added a solution of NaOH (0.37 g, 9.17 mmol) in H2O (1 ml). The reaction mixture was heated at 100° C. for 24 hrs and neutralized with 3N HCl. Ethanol was removed in vacuo and the remaining aqueous solution was extracted into methylene chloride. The combined extract was washed with water, dried over Na2SO4, filtered and concentrated. Flash chromatography on silica gel (3 to 8% EtOAc in Hexanes) gave 5-(4-Amino-2-ethylamino-pyrimidin-5-yloxy)-4-isopropyl-2-methoxy-benzamide (0.086 g, 27%) as a white solid. (M+H)=346.

Workup

  1. customEthanol was removed in vacuo
  2. extractionthe remaining aqueous solution was extracted into methylene chloride
  3. extractionThe combined extract
  4. washwas washed with water
  5. dry with materialdried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-c637dc8cdbad4f768ed1eae35d0afec5
Source dataset
uspto-grants-2014_09
Patent number
US08846705B2

Reaction notes

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