Ammonia → HCID 90102172, compound

HRID 1052546Notes

Reaction equation

HRID 1052546 reaction equation
[Cl:1][C:2]1[C:7]([C:8]([O:10][C:11]2[CH:16]=[C:15]([NH:17][S:18]([CH3:21])(=[O:20])=[O:19])[CH:14]=[C:13]([OH:22])[CH:12]=2)=[O:9])=[C:6](Cl)[N:5]=[CH:4][N:3]=1.[NH3:24]>O1CCOCC1>[NH2:24][C:6]1[C:7]([C:8]([O:10][C:11]2[CH:16]=[C:15]([NH:17][S:18]([CH3:21])(=[O:20])=[O:19])[CH:14]=[C:13]([OH:22])[CH:12]=2)=[O:9])=[C:2]([Cl:1])[N:3]=[CH:4][N:5]=1

Participants

4

Reactant 2

HCID 222AmmoniaHCID 90102725HCID 90102725, compound

Product 1

HCID 90102172HCID 90102172, compoundYield 70%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Conditions

Temperature
0 °C

Procedure

3-Hydroxy-5-(methylsulfonamido)phenyl 4,6-dichloropyrimidine-5-carboxylate (110 mg, 0.29 mmol) was dissolved in dioxane (5 ml) and cooled in an ice bath. Ammonia (0.86 ml, 7N in MeOH) was dropwise added and the mixture was stirred at 0° C. and overnight at room temperature. After dilution with ethyl acetate, this organic phase was successively washed with water and brine, dried over magnesium sulphate, filtered and the solvents evaporated under reduced pressure, to yield an oil as a residue (148 mg, 49% purity, 70% 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 successively 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 (148 mg, 49% purity, 70% yield) which
  7. customwas used in the next synthetic step without further purification

Sources & evidence

ORD record
ord-604b38a20421499eb009c878586dd5be
Source dataset
uspto-grants-2016_07
Patent number
US09388189B2

Reaction notes

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