Ammonia → 4-Amino-6-chloro-N-(3,5-dimethoxyphenyl)-5-pyrimidinecarboxamide

HRID 1052446Notes

Reaction equation

HRID 1052446 reaction equation
[Cl:1][C:2]1[C:7]([C:8]([NH:10][C:11]2[CH:16]=[C:15]([O:17][CH3:18])[CH:14]=[C:13]([O:19][CH3:20])[CH:12]=2)=[O:9])=[C:6](Cl)[N:5]=[CH:4][N:3]=1.[NH3:22]>O1CCOCC1>[NH2:22][C:6]1[C:7]([C:8]([NH:10][C:11]2[CH:16]=[C:15]([O:17][CH3:18])[CH:14]=[C:13]([O:19][CH3:20])[CH:12]=2)=[O:9])=[C:2]([Cl:1])[N:3]=[CH:4][N:5]=1

Participants

4

Reactant 2

HCID 222AmmoniaHCID 901035974,6-Dichloro-N-(3,5-dimethoxyphenyl)-5-pyrimidinecarboxamide

Product 1

HCID 901027364-Amino-6-chloro-N-(3,5-dimethoxyphenyl)-5-pyrimidinecarboxamideYield 100%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Conditions

Temperature
0 °C

Procedure

4,6-Dichloro-N-(3,5-dimethoxyphenyl)pyrimidine-5-carboxamide (684 mg, 1.21 mmol) was dissolved in dioxane (5 ml) and cooled in an ice bath. Ammonia solution (0.86 ml, 7N in MeOH) was added dropwise and the mixture was stirred at 0° C. for 6 h and overnight at room temperature. After dilution with ethyl acetate, this organic phase was washed with water and brine, dried over magnesium sulphate, filtered and the solvents evaporated under reduced pressure, to yield an oil as a residue (575 mg, 66% purity, 100% yield) which was used in the next synthetic step without further purification.

Workup

  1. temperaturecooled in an ice bath
  2. washAfter dilution with ethyl acetate, this organic phase was washed with water and brine
  3. dry with materialdried over magnesium sulphate
  4. filtrationfiltered
  5. customthe solvents evaporated under reduced pressure
  6. customto yield an oil as a residue (575 mg, 66% purity, 100% yield) which
  7. customwas used in the next synthetic step without further purification

Sources & evidence

ORD record
ord-6641367cbac34ae9879722a990b96bad
Source dataset
uspto-grants-2016_07
Patent number
US09388189B2

Reaction notes

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