2-Propanol, reaction products with ammonia, distn. residues → 4-(3-(4-methoxyphenyl)-6-(3-nitrophenyl)-1H-indol-1-yl)pyrimidin-2-amine

HRID 2192273Notes

Reaction equation

HRID 2192273 reaction equation
C(O)(C)C.[NH3:5].[CH3:6][O:7][C:8]1[CH:13]=[CH:12][C:11]([C:14]2[C:22]3[C:17](=[CH:18][C:19]([C:23]4[CH:28]=[CH:27][CH:26]=[C:25]([N+:29]([O-:31])=[O:30])[CH:24]=4)=[CH:20][CH:21]=3)[N:16]([C:32]3[CH:37]=[CH:36][N:35]=[C:34](S(C)=O)[N:33]=3)[CH:15]=2)=[CH:10][CH:9]=1>>[CH3:6][O:7][C:8]1[CH:13]=[CH:12][C:11]([C:14]2[C:22]3[C:17](=[CH:18][C:19]([C:23]4[CH:28]=[CH:27][CH:26]=[C:25]([N+:29]([O-:31])=[O:30])[CH:24]=4)=[CH:20][CH:21]=3)[N:16]([C:32]3[CH:37]=[CH:36][N:35]=[C:34]([NH2:5])[N:33]=3)[CH:15]=2)=[CH:10][CH:9]=1

Participants

3

Reactant 2

HCID 183319422-Propanol, reaction products with ammonia, distn. residuesHCID 509919253-(4-methoxyphenyl)-1-(2-(methylsulfinyl)pyrimidin-4-yl)-6-(3-nitrophenyl)-1H-indole

Product 1

HCID 509919264-(3-(4-methoxyphenyl)-6-(3-nitrophenyl)-1H-indol-1-yl)pyrimidin-2-amine

Conditions

Temperature
100 °C

Procedure

2.0 M ammonia isopropanol solution (2 mL) was added to 3-(4-methoxyphenyl)-1-(2-(methylsulfinyl)pyrimidin-4-yl)-6-(3-nitrophenyl)-1H-indole (90 mg) and then stirred at 100° C. for 3 hours in a sealed state. After cooling to room temperature, thus produced solid was filtered. After washing with isopropanol and then drying, the target compound (50 mg) was obtained as white solid.

Workup

  1. temperatureAfter cooling to room temperature
  2. filtrationthus produced solid was filtered
  3. washAfter washing with isopropanol
  4. customdrying

Sources & evidence

ORD record
ord-71e21845b3e74fac88e53e1bf84a7c23
Source dataset
uspto-grants-2012_12
Patent number
US08329708B2

Reaction notes

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