HCID 15158253, compound → HCID 15158254, compound

HRID 1646401Notes

Reaction equation

HRID 1646401 reaction equation
Cl[C:2]1[N:7]=[CH:6][N:5]=[C:4]([NH:8][N:9]2[C:21]3[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=3[C:15]3[C:10]2=[CH:11][CH:12]=[CH:13][CH:14]=3)[CH:3]=1>C(O)C.[Pd]>[N:7]1[CH:2]=[CH:3][C:4]([NH:8][N:9]2[C:21]3[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=3[C:15]3[C:10]2=[CH:11][CH:12]=[CH:13][CH:14]=3)=[N:5][CH:6]=1

Participants

4

Reactant 1

HCID 15158253HCID 15158253, compound

Product 1

HCID 15158254HCID 15158254, compoundYield 175.5%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent2×

Procedure

To a slurry of 10% Pd/C (1.0 g) and 0.8 g MgO in 5 ml of ethanol was added 4.0 g of N-(6-chloropyrimidin-4-yl)-9H-carbazol-9-amine in 12.0 ml of ethanol and the mixture was hydrogenated at atmospheric pressure at room temperature. When the reaction was complete, the mixture was filtered and the filtrate was evaporated to yield 6.2 g of an oil, which was preabsorbed on silica gel and eluted with 5% ethyl acetate/DCM on a silica gel column via the flash method. The desired fractions were evaporated to yield 2.4 g (61.5%) of a solid, N-(pyrimidin-4-yl)-9H-carbazol-9-amine, m.p. 177°-180° C.

Workup

  1. customwas hydrogenated at atmospheric pressure at room temperature
  2. filtrationthe mixture was filtered
  3. customthe filtrate was evaporated

Sources & evidence

ORD record
ord-53970b26786f41a7ae7d8175fbe0e81f
Source dataset
uspto-grants-1993_01
Patent number
US05179204

Reaction notes

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