HCID 68463273, compound → HCID 68461489, compound

HRID 501197Notes

Reaction equation

HRID 501197 reaction equation
[CH3:1][O:2][C:3]([C:5]1[CH:6]=[N:7][C:8]([N:11]2[CH2:26][CH2:25][C:14]3[NH:15][C:16]4[CH:17]=[CH:18][C:19]([N+:22]([O-])=O)=[CH:20][C:21]=4[C:13]=3[CH2:12]2)=[N:9][CH:10]=1)=[O:4]>CO.[Ni]>[CH3:1][O:2][C:3]([C:5]1[CH:6]=[N:7][C:8]([N:11]2[CH2:26][CH2:25][C:14]3[NH:15][C:16]4[CH:17]=[CH:18][C:19]([NH2:22])=[CH:20][C:21]=4[C:13]=3[CH2:12]2)=[N:9][CH:10]=1)=[O:4]

Participants

4

Reactant 1

HCID 68463273HCID 68463273, compound

Product 1

HCID 68461489HCID 68461489, compoundYield 43.9%

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 887MethanolSolvent

Procedure

To a solution of methyl-2-(8-nitro-1,3,4,5-tetrahydro-2H-pyrido[4,3-b]indol-2-yl)pyrimidine-5-carboxylate (0.5 g, 1.41 mmol) in methanol (50 mL) was added Raney Nickel (0.3 g). The reaction mixture was evacuated and stirred at rt under hydrogen atmosphere over night. The progress of the reaction was monitored by TLC and upon completion of the reaction, the mixture was filtered through celite under nitrogen atmosphere and washed with methanol (2×30 mL). The methanol was removed under reduced pressure to give crude residue which was purified by column chromatography to give the methyl-2-(8-amino-1,3,4,5-tetrahydro-2H-pyrido[4,3-b]indol-2-yl)pyrimidine-5-carboxylate (0.2 g, 43.9%); (Rt=12.46).

Workup

  1. customThe reaction mixture was evacuated
  2. customThe progress of the reaction was monitored by TLC and upon completion of the reaction
  3. filtrationthe mixture was filtered through celite under nitrogen atmosphere
  4. washwashed with methanol (2×30 mL)
  5. customThe methanol was removed under reduced pressure
  6. customto give crude residue which
  7. customwas purified by column chromatography

Sources & evidence

ORD record
ord-b76ad490e88d477caa3b2569c0059aa3
Source dataset
uspto-grants-2010_08
Patent number
US07772245B2

Reaction notes

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