Triethylamine → HCID 178441574, compound

HRID 219734Notes

Reaction equation

HRID 219734 reaction equation
[C:1]([C:5]1[N:10]=[C:9]([N:11]2[CH2:16][CH2:15][N:14]([CH2:17][CH2:18][CH2:19]Cl)[CH2:13][CH2:12]2)[CH:8]=[C:7]([CH:21]2[CH2:24][CH2:23][CH2:22]2)[N:6]=1)([CH3:4])([CH3:3])[CH3:2].[N:25]1[C:30]([OH:31])=[CH:29][C:28]([OH:32])=[N:27][CH:26]=1.C(N(CC)CC)C>CN(C)C=O>[C:1]([C:5]1[N:10]=[C:9]([N:11]2[CH2:16][CH2:15][N:14]([CH2:17][CH2:18][CH2:19][O:32][C:28]3[N:27]=[CH:26][N:25]=[C:30]([OH:31])[CH:29]=3)[CH2:13][CH2:12]2)[CH:8]=[C:7]([CH:21]2[CH2:24][CH2:23][CH2:22]2)[N:6]=1)([CH3:4])([CH3:3])[CH3:2]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 666731042-tert-Butyl-4-[4-(3-chloro-propyl)-piperazin-1-yl]-6-cyclobutyl-pyrimidineHCID 178516651HCID 178516651, compound

Product 1

HCID 178441574HCID 178441574, compoundYield 14.8%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

1.5 g of 2-tert-Butyl-4-[4-(3-chloro-propyl)-piperazin-1-yl]-6-cyclobutyl-pyrimidine (4.27 mmol), 0.72 g of pyrimidine-4,6-diol (6.4 mmol) and 1.31 g of triethylamine in 30 ml of dimethylformamide were stirred for 16 h at 80° C. The mixture was extracted with water and ethyl acetate. The organic layer was dried over magnesium sulfate, filtered, and concentrated to dryness. The crude product was purified by chromatography on silica gel using dichloromethane-methanol (1-10%). Fractions containing the product were combined. The solvents were evaporated and the oily residue was treated with acetonitrile. The precipitate was collected by filtration and dried to yield 0.27 g of the title compound.

Workup

  1. extractionThe 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. customThe crude product was purified by chromatography on silica gel
  6. additionFractions containing the product
  7. customThe solvents were evaporated
  8. additionthe oily residue was treated with acetonitrile
  9. filtrationThe precipitate was collected by filtration
  10. customdried

Sources & evidence

ORD record
ord-52ff1e4a31314812a52f6027fa63d294
Source dataset
uspto-grants-2012_06
Patent number
US08202868B2

Reaction notes

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