Ammonium Hydroxide → HCID 57928091, compound

HRID 2233214Notes

Reaction equation

HRID 2233214 reaction equation
[Cl:1][C:2]1[C:7]([CH2:8][CH2:9][C:10](OCC)=[O:11])=[C:6](Cl)[N:5]=[C:4](/[CH:16]=[CH:17]/[C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[N:3]=1.[NH4+:24].[OH-]>O1CCOCC1>[Cl:1][C:2]1[C:7]2[CH2:8][CH2:9][C:10](=[O:11])[NH:24][C:6]=2[N:5]=[C:4](/[CH:16]=[CH:17]/[C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[N:3]=1

Participants

4

Reactant 2

HCID 14923Ammonium HydroxideHCID 86628367HCID 86628367, compound

Product 1

HCID 57928091HCID 57928091, compoundYield 21%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Conditions

Temperature
75 °C

Procedure

To a solution of ethyl 3-{4,6-dichloro-2-[(E)-2-phenylethenyl]-5-pyrimidinyl}propanoate (0.42 g, 1.19 mmol) in 1,4-dioxane (5 mL) was added conc. NH4OH (3.5 mL). The reaction was heated at 75° C. in a sealed tube for 16 h. The solution was concentrated under vacuum, diluted with water, and extracted with EtOAc. The organic layer was washed with brine, dried over Na2SO4, and concentrated under vacuum. The crude residue was then purified by column chromatography (silica gel) to yield the desired compound as a yellow solid (0.072 g, 21%).

Workup

  1. concentrationThe solution was concentrated under vacuum
  2. additiondiluted with water
  3. extractionextracted with EtOAc
  4. washThe organic layer was washed with brine
  5. dry with materialdried over Na2SO4
  6. concentrationconcentrated under vacuum
  7. customThe crude residue was then purified by column chromatography (silica gel)

Sources & evidence

ORD record
ord-3def694121644609b060f5113f135185
Source dataset
uspto-grants-2010_05
Patent number
US07709483B2

Reaction notes

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