HCID 54166420, compound → HCID 54089172, compound

HRID 1611894Notes

Reaction equation

HRID 1611894 reaction equation
[CH2:1]([N:8]1[CH2:13][CH2:12][NH:11][CH2:10][CH:9]1[C:14]1[N:19]=[C:18]([CH:20]2[CH2:25][NH:24][CH2:23][CH2:22][N:21]2[CH2:26][C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)[CH:17]=[C:16]([NH:33]N)[N:15]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1>CCOC(C)=O.[Ni]>[CH2:1]([N:8]1[CH2:13][CH2:12][NH:11][CH2:10][CH:9]1[C:14]1[N:19]=[C:18]([CH:20]2[CH2:25][NH:24][CH2:23][CH2:22][N:21]2[CH2:26][C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)[CH:17]=[C:16]([NH2:33])[N:15]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 1

HCID 54166420HCID 54166420, compound

Product 1

HCID 54089172HCID 54089172, compoundYield 94.4%

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 8857Ethyl AcetateSolvent

Procedure

A suspension of 2,4-di(N-benzylpiperazinyl)-6-hydrazino pyrimidine (19.7 g, 43 mmol) and Raney Ni (5 g) in EtOAc (250 mL) was shaken in a Parr hydrogenator at 50 psi H2 for 16 hours. The resulting suspension was filtered through celite and the filtrate was concentrated to give 18 g (94%) of the title compound as a foam. 1H NMR (CDCl3) δ 2.47 (m, 8H, piperazine), 3.51 (m, 8H, piperazine), 3.77 (m, 4H, CH2), 4.30 (bs, 2H, NH2), 5.04 (s, 1H, C5H), 7.3 (m, 10H, Ar).

Workup

  1. filtrationThe resulting suspension was filtered through celite
  2. concentrationthe filtrate was concentrated

Sources & evidence

ORD record
ord-4bd35e73b4b1490ebcc322f460189faa
Source dataset
uspto-grants-2006_01
Patent number
US06991902B2

Reaction notes

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