Hydrazine → HCID 54166420, compound

HRID 1611893Notes

Reaction equation

HRID 1611893 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](Cl)[N:15]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[NH2:34][NH2:35]>O1CCOCC1>[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:34][NH2:35])[N:15]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 9321HydrazineHCID 54564214HCID 54564214, compound

Product 1

HCID 54166420HCID 54166420, compoundYield 97%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

A solution of 2,4-di(N-benzylpiperazinyl)-6-chloropyrimidine (48.4 g, 104 mmol), hydrazine (96 g, 3 mol), in p-dioxane (1000 mL) was heated at 75° C. for 16 hours. The reaction was concentrated, dissolved in CH2-Cl2, washed with H2O, and dried (MgSO4). Filtration and concentration of the resulting solution gave 46 g (97%) of the title compound as a foam. 1H NMR (CDCl3) δ 2.44 (m, 8H, piperazine), 3.52-3.59 (m, 8H, piperazine), 3.71 (m, 4H, CH2), 5.22 (s, 1H, C5H), 5.72 (bs, 2H, NH2), 7.30 (m, 10H, Ar).

Workup

  1. concentrationThe reaction was concentrated
  2. dissolutiondissolved in CH2-Cl2
  3. washwashed with H2O
  4. dry with materialdried (MgSO4)
  5. filtrationFiltration and concentration of the resulting solution

Sources & evidence

ORD record
ord-f783b372ff4945149d59f7b71306f870
Source dataset
uspto-grants-2006_01
Patent number
US06991902B2

Reaction notes

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