Ammonia → HCID 67204099, compound

HRID 1615384Notes

Reaction equation

HRID 1615384 reaction equation
[NH3:1].CS([C:5]1[N:10]=[C:9]([N:11]2[C:19]3[C:14](=[CH:15][CH:16]=[C:17]([C:20]4[CH:25]=[CH:24][CH:23]=[C:22]([N+:26]([O-:28])=[O:27])[CH:21]=4)[CH:18]=3)[CH:13]=[CH:12]2)[CH:8]=[CH:7][N:6]=1)=O.O>C(O)(C)C>[N+:26]([C:22]1[CH:21]=[C:20]([C:17]2[CH:18]=[C:19]3[C:14]([CH:13]=[CH:12][N:11]3[C:9]3[CH:8]=[CH:7][N:6]=[C:5]([NH2:1])[N:10]=3)=[CH:15][CH:16]=2)[CH:25]=[CH:24][CH:23]=1)([O-:28])=[O:27]

Participants

5

Reactant 3

HCID 222AmmoniaHCID 962WaterHCID 67204402HCID 67204402, compound

Product 1

HCID 67204099HCID 67204099, compound

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Conditions

Temperature
100 °C

Procedure

Ammonia solution (2.0 M in isopropanol) was added to 1-(2-(methylsulfinyl)pyrimidin-4-yl)-6-(3-nitrophenyl)-1H-indole (102 mg) dissolved in isopropanol. After stirring at 100° C. for 3 hours and cooling to room temperature, the reaction mixture was added to water. The aqueous layer was extracted with ethyl acetate. The combined organic layer was washed with brine, dried with magnesium sulfate, and concentrated under reduced pressure. 4-(6-(3-Nitrophenyl)-1H-indol-1-yl)pyrimidin-2-amine (76.8 mg) was yielded.

Workup

  1. temperaturecooling to room temperature
  2. extractionThe aqueous layer was extracted with ethyl acetate
  3. washThe combined organic layer was washed with brine
  4. dry with materialdried with magnesium sulfate
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-b0fe77bc7ef7464bbc90b76a4478fc15
Source dataset
uspto-grants-2014_07
Patent number
US08765749B2

Reaction notes

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