4-[4-((R)-1-Phenyl-ethylamino)-7H-pyrrolo[2,3-d]pyrimidin-6-yl]-benzonitrile → [6-(4-Aminomethyl-phenyl)-7H-pyrrolo[2,3-d]pyrimidin-4-yl]-((R)-1-phenyl-ethyl)-amine

HRID 133031Notes

Reaction equation

HRID 133031 reaction equation
[C:1]1([C@H:7]([NH:9][C:10]2[C:11]3[CH:18]=[C:17]([C:19]4[CH:26]=[CH:25][C:22]([C:23]#[N:24])=[CH:21][CH:20]=4)[NH:16][C:12]=3[N:13]=[CH:14][N:15]=2)[CH3:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1>N.CO.C1COCC1.[Ni]>[NH2:24][CH2:23][C:22]1[CH:25]=[CH:26][C:19]([C:17]2[NH:16][C:12]3[N:13]=[CH:14][N:15]=[C:10]([NH:9][C@@H:7]([C:1]4[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=4)[CH3:8])[C:11]=3[CH:18]=2)=[CH:20][CH:21]=1

Participants

6

Reactant 1

HCID 573997444-[4-((R)-1-Phenyl-ethylamino)-7H-pyrrolo[2,3-d]pyrimidin-6-yl]-benzonitrile

Product 1

HCID 59756727[6-(4-Aminomethyl-phenyl)-7H-pyrrolo[2,3-d]pyrimidin-4-yl]-((R)-1-phenyl-ethyl)-amine

Reagents, catalysts & solvents 4

HCID 935NickelCatalystHCID 222AmmoniaSolventHCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

Raney-Nickel (0.1 9) catalyzed hydrogenation of 0.206 g (0.6 mmol) 4-[4-((R)-1-phenyl-ethylamino)-7H-pyrrolo[2,3-d]pyrimidin-6-yl]-benzonitrile in a mixture of 5% ammonia in methanol (20 ml) and THF (4 ml) for 6 h at atmospheric pressure followed by filtration and evaporation of the solvent gives the title compound; m.p. 253-256° C.; MS-ES+: (M+H)+=344.

Workup

  1. filtrationfollowed by filtration and evaporation of the solvent

Sources & evidence

ORD record
ord-18bbe7d7500642e0bcdff501a085c687
Source dataset
uspto-grants-2008_06
Patent number
US07390805B2

Reaction notes

Loading…