HCID 178513385, compound → HCID 67055938, compound

HRID 2036833Notes

Reaction equation

HRID 2036833 reaction equation
O[NH:2][C:3](=N)[C:4]1[CH:9]=[C:8]([C:10]2[N:19]=[C:18]([NH:20][CH2:21][C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][N:23]=3)[C:17]3[C:12](=[CH:13][CH:14]=[CH:15][C:16]=3[C:28]3[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=3)[N:11]=2)[CH:7]=[N:6][CH:5]=1>N.CO.[Ni]>[NH2:2][CH2:3][C:4]1[CH:9]=[C:8]([C:10]2[N:19]=[C:18]([NH:20][CH2:21][C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][N:23]=3)[C:17]3[C:12](=[CH:13][CH:14]=[CH:15][C:16]=3[C:28]3[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=3)[N:11]=2)[CH:7]=[N:6][CH:5]=1

Participants

5

Reactant 1

HCID 178513385HCID 178513385, compound

Product 1

HCID 67055938HCID 67055938, compoundYield 50%

Reagents, catalysts & solvents 3

HCID 935NickelCatalystHCID 222AmmoniaSolventHCID 887MethanolSolvent

Procedure

To a solution of 5-(5-phenyl-4-(pyridin-2-ylmethylamino)quinazolin-2-yl)nicotinonitrile (from example 183: 200 mg, 0.48 mmol) in 5% ammonia in methanol (5 mL) was added Ra—Ni (catalytic) and the resulting slurry was stirred under hydrogen atmosphere for 16 h. After this time, the reaction mixture was filtered and the filtrate was concentrated under reduced pressure to yield 2-(5-(aminomethyl)pyridin-3-yl)-5-phenyl-N-(pyridin-2-ylmethyl)quinazolin-4-amine (0.1 g, 50% yield), which was used without further purification.

Workup

  1. filtrationAfter this time, the reaction mixture was filtered
  2. concentrationthe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-14fc699c82d34d048b8ca601ee2b2bc4
Source dataset
uspto-grants-2013_11
Patent number
US08575184B2

Reaction notes

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