Ammonia → HCID 90102281, compound

HRID 1052461Notes

Reaction equation

HRID 1052461 reaction equation
[Cl:1][C:2]1[C:7]([C:8]([NH:10][C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=2[O:17][CH3:18])=[O:9])=[C:6](Cl)[N:5]=[CH:4][N:3]=1.[NH3:20]>O1CCOCC1>[NH2:20][C:6]1[C:7]([C:8]([NH:10][C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=2[O:17][CH3:18])=[O:9])=[C:2]([Cl:1])[N:3]=[CH:4][N:5]=1

Participants

4

Reactant 2

HCID 222AmmoniaHCID 901027264,6-Dichloro-N-(2-methoxyphenyl)-5-pyrimidinecarboxamide

Product 1

HCID 90102281HCID 90102281, compoundYield 95.8%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Conditions

Temperature
0 °C

Procedure

4,6-Dichloro-N-(2-methoxyphenyl)pyrimidine-5-carboxamide (506 mg, 1.70 mmol) was dissolved in dioxane (8 ml) and cooled in an ice bath. Ammonia solution (1.25 ml, 8.75 mmol, 7N in MeOH) was added dropwise and the mixture was stirred at 0° C. for 6 h. After evaporation of the solvent under reduced pressure, the residue was suspended in ethyl acetate and filtered, washing successively with ethyl acetate. The solvent of the filtrate is evaporated under reduced pressure to yield the final compound as a solid (454 mg, 93% purity, 89% yield) which was used in the next synthetic step without further purification.

Workup

  1. temperaturecooled in an ice bath
  2. customAfter evaporation of the solvent under reduced pressure
  3. filtrationfiltered
  4. washwashing successively with ethyl acetate
  5. customThe solvent of the filtrate is evaporated under reduced pressure

Sources & evidence

ORD record
ord-bf189cd303504b40af94458340927287
Source dataset
uspto-grants-2016_07
Patent number
US09388189B2

Reaction notes

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