1,1'-Carbonyldiimidazole → 1-[2-(1-Adamantyl)ethyl]-3-[3-(4-pyridyl)propyl]hexahydropyrimidin-2-one

HRID 2075905Notes

Reaction equation

HRID 2075905 reaction equation
[C:1]12([CH2:11][CH2:12][NH:13][CH2:14][CH2:15][CH2:16][NH:17][CH2:18][CH2:19][CH2:20][C:21]3[CH:26]=[CH:25][N:24]=[CH:23][CH:22]=3)[CH2:10][CH:5]3[CH2:6][CH:7]([CH2:9][CH:3]([CH2:4]3)[CH2:2]1)[CH2:8]2.[C:27](N1C=CN=C1)(N1C=CN=C1)=[O:28]>C(Cl)Cl>[C:1]12([CH2:11][CH2:12][N:13]3[CH2:14][CH2:15][CH2:16][N:17]([CH2:18][CH2:19][CH2:20][C:21]4[CH:22]=[CH:23][N:24]=[CH:25][CH:26]=4)[C:27]3=[O:28])[CH2:2][CH:3]3[CH2:4][CH:5]([CH2:6][CH:7]([CH2:9]3)[CH2:8]1)[CH2:10]2

Participants

4

Reactant 2

HCID 682631,1'-CarbonyldiimidazoleHCID 21974043N-[2-(1-adamantyl)ethyl]-N'-[3-(4-pyridyl)propyl]-1,3-propanediamine

Product 1

HCID 219739651-[2-(1-Adamantyl)ethyl]-3-[3-(4-pyridyl)propyl]hexahydropyrimidin-2-oneYield 9.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent3×

Procedure

To anhydrous methylene chloride (50 ml) were added a solution of the obtained. N-[2-(1-adamantyl)ethyl]-N′-[3-(4-pyridyl)propyl]-1,3-propanediamine (80 mg, 0.23 mmol) in anhydrous methylene chloride (10 ml) and a solution of 1,1′-carbonyldiimidazole (40 mg, 0.26 mmol) in anhydrous methylene chloride (10 ml) dropwise simultaneously with stirring at room temperature over 20 minutes. The mixture was stirred overnight, the reaction mixture was concentrated under reduced pressure, and the residue was purified by silica gel column chromatography to give 8.0 mg (9.4%) of the titled compound.

Workup

  1. concentrationthe reaction mixture was concentrated under reduced pressure
  2. customthe residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-d980e5b0c79240d3ada6c5e90bff2e7e
Source dataset
uspto-grants-2011_04
Patent number
US07923461B2

Reaction notes

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