Hydrazine hydrate (1:1) → 2-{1-[4-(2-Amino-ethyl)-2-p-tolyl-imidazol-1-yl]-2-methyl-propyl}-3-benzyl-5,6-dimethyl-3H-pyrimidin-4-one

HRID 1374874Notes

Reaction equation

HRID 1374874 reaction equation
[CH2:1]([N:8]1[C:13](=[O:14])[C:12]([CH3:15])=[C:11]([CH3:16])[N:10]=[C:9]1[CH:17]([N:21]1[CH:25]=[C:24]([CH2:26][CH2:27][N:28]2C(=O)C3C(=CC=CC=3)C2=O)[N:23]=[C:22]1[C:39]1[CH:44]=[CH:43][C:42]([CH3:45])=[CH:41][CH:40]=1)[CH:18]([CH3:20])[CH3:19])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.O.NN>CCO>[NH2:28][CH2:27][CH2:26][C:24]1[N:23]=[C:22]([C:39]2[CH:40]=[CH:41][C:42]([CH3:45])=[CH:43][CH:44]=2)[N:21]([CH:17]([C:9]2[N:8]([CH2:1][C:2]3[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=3)[C:13](=[O:14])[C:12]([CH3:15])=[C:11]([CH3:16])[N:10]=2)[CH:18]([CH3:20])[CH3:19])[CH:25]=1

Participants

4

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 210769262-(2-{1-[1-(1-Benzyl-4,5-dimethyl-6-oxo-1,6-dihydro-pyrimidin-2-yl)-2-methyl-propyl]-2-p-tolyl-1H-imidazol-4-yl}-ethyl)-isoindole-1,3-dione

Product 1

HCID 103899522-{1-[4-(2-Amino-ethyl)-2-p-tolyl-imidazol-1-yl]-2-methyl-propyl}-3-benzyl-5,6-dimethyl-3H-pyrimidin-4-oneYield 72%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To 2-(2-{1-[1-(1-Benzyl-4,5-dimethyl-6-oxo-1,6-dihydro-pyrimidin-2-yl)-2-methyl-propyl]-2-p-tolyl-1H-imidazol-4yl}-ethyl)-isoindole-1,3-dione (0.371 g, 0.619 mmol) in EtOH (14 mL) was added hydrazine monohydrate (0.138 g, 2.48 mmol) and the reaction was stirred at room temperature for 72 h. The reaction was filtered and the filtrate was concentrated to dryness. The residue was purified by flash chromatography on silica gel (90:9:1 CH2Cl2:MeOH:NH4OH) to give the title compound as a white solid (0.209 g, 72%). MS(ES)+m/e 470 [M+H]+.

Workup

  1. filtrationThe reaction was filtered
  2. concentrationthe filtrate was concentrated to dryness
  3. customThe residue was purified by flash chromatography on silica gel (90:9:1 CH2Cl2:MeOH:NH4OH)

Sources & evidence

ORD record
ord-7dbc9bb18e9d4435a20c7e57d97fe714
Source dataset
uspto-grants-2007_01
Patent number
US07166595B2

Reaction notes

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