Ammonium Hydroxide → HCID 66984885, compound

HRID 1950778Notes

Reaction equation

HRID 1950778 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([NH:11][C:12]2[C:17]([C:18](OCC)=[O:19])=[C:16](/[CH:23]=[CH:24]/[N:25](C)C)[N:15]=[C:14]([S:28][CH3:29])[N:13]=2)[CH:6]=[C:7]([O:9][CH3:10])[CH:8]=1.[NH4+].[OH-]>CCO>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([NH:11][C:12]2[C:17]3[C:18](=[O:19])[NH:25][CH:24]=[CH:23][C:16]=3[N:15]=[C:14]([S:28][CH3:29])[N:13]=2)[CH:6]=[C:7]([O:9][CH3:10])[CH:8]=1

Participants

4

Reactant 2

HCID 14923Ammonium HydroxideHCID 86658932HCID 86658932, compound

Product 1

HCID 66984885HCID 66984885, compoundYield 56.5%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
80 °C

Procedure

The crude of (E)-ethyl 4-(3,5-dimethoxyphenylamino)-6-(2-(dimethylamino)vinyl)-2-(methylthio)pyrimidine-5-carboxylate (3.16 g) was dissolved in 45 mL EtOH. To the solution was added 30% NH4OH solution (5.2 mL), the reaction mixture was stirred at 75-85° C. for 10 hours. The mixture was cooled to room temperature. The solids formed from the solution were filtered. The filtrate was condensed under reduced pressure resulting in the solid residue. The residue was recrystallized from ethyl acetate. The combined solids were dried under reduced pressure yielding light yellow solids (1.47 g). MS m/z: 344.9 (M+H)+.

Workup

  1. temperatureThe mixture was cooled to room temperature
  2. customThe solids formed from the solution
  3. filtrationwere filtered
  4. customcondensed under reduced pressure
  5. customresulting in the solid residue
  6. customThe residue was recrystallized from ethyl acetate
  7. customThe combined solids were dried under reduced pressure

Sources & evidence

ORD record
ord-5601a8c9ee33490b8f1a14e43a101fa6
Source dataset
uspto-grants-2013_03
Patent number
US08404677B2

Reaction notes

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