Diisopropylethylamine → 1-{4-[4-(2,4-Dichlorobenzyl)piperazin-1-yl]butyl}-5-methyl-1H-pyrimidine-2,4-dione

HRID 1640459

Reaction equation

HRID 1640459 reaction equation
Cl[CH2:2][CH2:3][CH2:4][CH2:5][N:6]1[CH:11]=[C:10]([CH3:12])[C:9](=[O:13])[NH:8][C:7]1=[O:14].[Cl:15][C:16]1[CH:28]=[C:27]([Cl:29])[CH:26]=[CH:25][C:17]=1[CH2:18][N:19]1[CH2:24][CH2:23][NH:22][CH2:21][CH2:20]1.[Br-].[Na+].C(N(C(C)C)CC)(C)C>CN1CCCC1=O>[Cl:15][C:16]1[CH:28]=[C:27]([Cl:29])[CH:26]=[CH:25][C:17]=1[CH2:18][N:19]1[CH2:20][CH2:21][N:22]([CH2:2][CH2:3][CH2:4][CH2:5][N:6]2[CH:11]=[C:10]([CH3:12])[C:9](=[O:13])[NH:8][C:7]2=[O:14])[CH2:23][CH2:24]1

Participants

6

Reactant 4

HCID 81531DiisopropylethylamineHCID 253881Sodium BromideHCID 4111791-(2,4-Dichlorobenzyl)piperazineHCID 593375871-(4-chlorobutyl)-5-methylpyrimidine-2,4(1H,3H)-dione

Product 1

HCID 117188101-{4-[4-(2,4-Dichlorobenzyl)piperazin-1-yl]butyl}-5-methyl-1H-pyrimidine-2,4-dioneYield 33.4%

Reagents, catalysts & solvents 1

HCID 13387N-methyl-2-pyrrolidoneSolvent

Procedure

1-(4-Chlorobutyl)-5-methyl-1H-pyrimidine-2,4-dione (0.69 mmol, 0.15 g), 1-(2,4-dichlorobenzyl)piperazine (0.62 mmol, 0.15 g), sodium bromide (3.46 mmol, 0.36 g) and diisopropylethylamine (6.92 mmol, 0.89 g) were heated in N-methylpyrrolidinone (0.6 ml) at 120° C. for 5 hours. The reaction mixture was then allowed to cool, the suspension was filtered with suction, and the filtrate was concentrated. The residue was then then taken up in ethyl acetate and washed with saturated brine. The organic layer was dried, filtered to remove the desiccant and evaporated in vacuo. The resulting residue was purified by chromatography on silica gel (eluent: methyl tert-butyl ether/methanol (0-100%), resulting in 88.0 mg of the title compound.

Workup

  1. temperatureto cool
  2. filtrationthe suspension was filtered with suction
  3. concentrationthe filtrate was concentrated
  4. washwashed with saturated brine
  5. customThe organic layer was dried
  6. filtrationfiltered
  7. customto remove the desiccant and
  8. customevaporated in vacuo
  9. customThe resulting residue was purified by chromatography on silica gel (eluent

Sources & evidence

ORD record
ord-85ba6cec0af0423ba4949588bab461f4
Source dataset
uspto-grants-2012_02
Patent number
US08114875B2

Linked notes

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