Ammonium Hydroxide → HCID 57928091, compound

HRID 657107Notes

Reaction equation

HRID 657107 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 overnight. The solution was concentrated under vacuum, diluted with water, and extracted with EtOAc/DCM. 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 (0.072 g, 21%). LCMS: m/z 286.2 (MH+). Also obtained was 3-{4-amino-6-chloro-2-[(E)-2-phenylethenyl]-5-pyrimidinyl}propanamide (0.175 g).

Workup

  1. concentrationThe solution was concentrated under vacuum
  2. additiondiluted with water
  3. extractionextracted with EtOAc/DCM
  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-2f151a6b2fe84c848991ec160ef1a758
Source dataset
uspto-grants-2011_12
Patent number
US08071592B2

Reaction notes

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