Stannous chloride dihydrate → HCID 67203814, compound

HRID 1615385Notes

Reaction equation

HRID 1615385 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]([C:10]2[CH:18]=[C:17]3[C:13]([CH:14]=[CH:15][N:16]3[C:19]3[CH:24]=[CH:23][N:22]=[C:21]([NH2:25])[N:20]=3)=[CH:12][CH:11]=2)[CH:7]=[CH:8][CH:9]=1)([O-])=O.O.O.Cl[Sn]Cl.C(=O)(O)[O-].[Na+]>C(O)C>[NH2:1][C:4]1[CH:5]=[C:6]([C:10]2[CH:18]=[C:17]3[C:13]([CH:14]=[CH:15][N:16]3[C:19]3[CH:24]=[CH:23][N:22]=[C:21]([NH2:25])[N:20]=3)=[CH:12][CH:11]=2)[CH:7]=[CH:8][CH:9]=1

Participants

5

Reactant 3

HCID 61436Stannous chloride dihydrateHCID 516892Sodium BicarbonateHCID 67204099HCID 67204099, compound

Product 1

HCID 67203814HCID 67203814, compoundYield 60.1%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
100 °C

Procedure

4-(6-(3-Nitrophenyl)-1H-indol-1-yl)pyrimidin-2-amine (76.8 mg, 0.232 mmol) was dissolved in ethanol and, after adding SnCl2.2H2O (262 mg, 1.159 mmol), the mixture was stirred at 100° C. for 3 hours. The reaction mixture was added to sodium bicarbonate aqueous solution and extracted with ethyl acetate. The combined organic layer was washed with brine, dried with magnesium sulfate, and concentrated under reduced pressure. Purification of the residue by column chromatography (silica gel, MC:MeOH=20:1) yielded 4-(6-(3-aminophenyl)-1H-indol-1-yl)pyrimidin-2-amine (42 mg).

Workup

  1. extractionextracted with ethyl acetate
  2. washThe combined organic layer was washed with brine
  3. dry with materialdried with magnesium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customPurification of the residue by column chromatography (silica gel, MC:MeOH=20:1)

Sources & evidence

ORD record
ord-5a34d0230e01428587baa884e43bc91d
Source dataset
uspto-grants-2014_07
Patent number
US08765749B2

Reaction notes

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