Stannous chloride dihydrate → HCID 67203963, compound

HRID 1615380Notes

Reaction equation

HRID 1615380 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([N+:8]([O-])=O)=[CH:4][C:3]=1[C:11]1[CH:19]=[C:18]2[C:14]([CH:15]=[CH:16][N:17]2[C:20]2[N:25]=[CH:24][N:23]=[C:22]([NH2:26])[CH:21]=2)=[CH:13][CH:12]=1.O.O.Cl[Sn]Cl.C(=O)(O)[O-].[Na+]>C(O)C>[NH2:8][C:5]1[CH:6]=[CH:7][C:2]([CH3:1])=[C:3]([C:11]2[CH:19]=[C:18]3[C:14]([CH:15]=[CH:16][N:17]3[C:20]3[N:25]=[CH:24][N:23]=[C:22]([NH2:26])[CH:21]=3)=[CH:13][CH:12]=2)[CH:4]=1

Participants

5

Reactant 3

HCID 61436Stannous chloride dihydrateHCID 516892Sodium BicarbonateHCID 67203510HCID 67203510, compound

Product 1

HCID 67203963HCID 67203963, compoundYield 69.3%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
100 °C

Procedure

6-(6-(2-Methyl-5-nitrophenyl)-1H-indol-1-yl)pyrimidin-4-amine (130 mg, 0.38 mmol) was dissolved in ethanol and, after adding SnCl2.2H2O (425 mg, 1.88 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 6-(6-(5-amino-2-methylphenyl)-1H-indol-1-yl)pyrimidin-4-amine (83 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-b9cf8efd23ed43588ef96c0c7bf4dd55
Source dataset
uspto-grants-2014_07
Patent number
US08765749B2

Reaction notes

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