Ammonia → HCID 90103324, compound

HRID 1052641Notes

Reaction equation

HRID 1052641 reaction equation
[Cl:1][C:2]1[C:7]([C:8]([NH:10][C:11]2[CH:16]=[C:15]([NH:17][S:18]([CH3:21])(=[O:20])=[O:19])[CH:14]=[C:13]([O:22][CH3:23])[CH:12]=2)=[O:9])=[C:6](Cl)[N:5]=[CH:4][N:3]=1.[NH3:25]>O1CCOCC1>[NH2:25][C:6]1[C:7]([C:8]([NH:10][C:11]2[CH:16]=[C:15]([NH:17][S:18]([CH3:21])(=[O:20])=[O:19])[CH:14]=[C:13]([O:22][CH3:23])[CH:12]=2)=[O:9])=[C:2]([Cl:1])[N:3]=[CH:4][N:5]=1

Participants

4

Reactant 2

HCID 222AmmoniaHCID 901021774,6-Dichloro-N-(3-methoxy-5-(methylsulfonamido)phenyl)pyrimidine-5-carboxamide

Product 1

HCID 90103324HCID 90103324, compoundYield 155.7%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Conditions

Temperature
0 °C

Procedure

4,6-Dichloro-N-(3-methoxy-5-(methylsulfonamido)phenyl)pyrimidine-5-carboxamide (617 mg, 73% purity, 1.14 mmol) was dissolved in dioxane (5 ml) and cooled in an ice bath. Ammonia (819 μl, 7N in MeOH, 5.7 mmol) was added dropwise and the mixture stirred at 0° C. for 6 h and at room temperature overnight. The solvent was removed and ethyl acetate added. The solid precipitate was filtered off and the filtrate was concentrated to give 660 mg (100% yield) of the title compound as an oil that was used in the next step without further purification. Purity 65%

Workup

  1. temperaturecooled in an ice bath
  2. customThe solvent was removed
  3. additionethyl acetate added
  4. filtrationThe solid precipitate was filtered off
  5. concentrationthe filtrate was concentrated

Sources & evidence

ORD record
ord-e57255a6e0174b41a4ad203abf1734d1
Source dataset
uspto-grants-2016_07
Patent number
US09388189B2

Reaction notes

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