Triethylamine → 2-{4-[4-(2-tert-Butyl-6-cyclobutyl-pyrimidin-4-yl)-piperazin-1-yl]-butyl}-isoindole-1,3-dione

HRID 219698Notes

Reaction equation

HRID 219698 reaction equation
[C:1]([C:5]1[N:10]=[C:9]([N:11]2[CH2:16][CH2:15][NH:14][CH2:13][CH2:12]2)[CH:8]=[C:7]([CH:17]2[CH2:20][CH2:19][CH2:18]2)[N:6]=1)([CH3:4])([CH3:3])[CH3:2].Br[CH2:22][CH2:23][CH2:24][CH2:25][N:26]1[C:30](=[O:31])[C:29]2=[CH:32][CH:33]=[CH:34][CH:35]=[C:28]2[C:27]1=[O:36].C(N(CC)CC)C>CN(C)C=O>[C:1]([C:5]1[N:10]=[C:9]([N:11]2[CH2:12][CH2:13][N:14]([CH2:22][CH2:23][CH2:24][CH2:25][N:26]3[C:30](=[O:31])[C:29]4[C:28](=[CH:35][CH:34]=[CH:33][CH:32]=4)[C:27]3=[O:36])[CH2:15][CH2:16]2)[CH:8]=[C:7]([CH:17]2[CH2:20][CH2:19][CH2:18]2)[N:6]=1)([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 93575N-(4-Bromobutyl)phthalimideHCID 666733902-tert-Butyl-4-cyclobutyl-6-(piperazin-1-yl)pyrimidine

Product 1

HCID 690260812-{4-[4-(2-tert-Butyl-6-cyclobutyl-pyrimidin-4-yl)-piperazin-1-yl]-butyl}-isoindole-1,3-dioneYield 21.9%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

1.45 g of 2-tert-butyl-4-(piperazin-1-yl)-6-cyclobutyl-pyrimidine (5.28 mmol), 1.5 g of N-(4-bromobutyl)phthalimid (5.28 mmol) and 0.8 g of triethylamine (7.9 mmol) were dissolved in 20 ml of dimethylformamide and stirred for 16 h at room temperature. The reaction mixture was extracted with water and ethyl acetate. The organic layer was dried over magnesium sulfate, filtered, and concentrated to dryness. The oily residue began to crystallise upon standing, was stirred with acetonitrile, and finally filtered to yield 0.55 g of the title compound.

Workup

  1. extractionThe reaction mixture was extracted with water and ethyl acetate
  2. dry with materialThe organic layer was dried over magnesium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated to dryness
  5. customto crystallise
  6. stirringwas stirred with acetonitrile
  7. filtrationfinally filtered

Sources & evidence

ORD record
ord-0b1423048fff409e937542e64b3af89a
Source dataset
uspto-grants-2012_06
Patent number
US08202868B2

Reaction notes

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