Ethylene → HCID 178436602, compound

HRID 1458654Notes

Reaction equation

HRID 1458654 reaction equation
[C:1]([C@@H:5]1[CH2:10][CH2:9][C@H:8]([NH:11][C:12]2[C:17](I)=[C:16]([CH2:19][CH3:20])[N:15]=[CH:14][N:13]=2)[CH2:7][CH2:6]1)([CH3:4])([CH3:3])[CH3:2].C=C.[C:23]([O-])(=O)[CH3:24].[K+]>CO.[Pd]>[C:1]([C@@H:5]1[CH2:10][CH2:9][C@H:8]([NH:11][C:12]2[C:17]([CH:23]=[CH2:24])=[C:16]([CH2:19][CH3:20])[N:15]=[CH:14][N:13]=2)[CH2:7][CH2:6]1)([CH3:4])([CH3:3])[CH3:2]

Participants

6

Reactant 3

HCID 6325EthyleneHCID 517044Potassium AcetateHCID 178437728HCID 178437728, compound

Product 1

HCID 178436602HCID 178436602, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

3.9 g (10 mmol) of 4-(cis-4-tert-butylcyclohexylamino)-6-ethyl-5-iodopyrimidine (Example 1) were treated with 10 bar of ethylene in an autoclave at 120° C. in the presence of 1.5 g (15 mmol) of potassium acetate and 50 mg of palladium black in 100 ml of methanol. After 24 hours, the catalyst was removed by filtration and the mixture was concentrated. Chromatography on silica gel gave 1.70 g (61.8% of theory) of colorless oil.

Workup

  1. customthe catalyst was removed by filtration
  2. concentrationthe mixture was concentrated
  3. customChromatography on silica gel gave 1.70 g (61.8% of theory) of colorless oil

Sources & evidence

ORD record
ord-22ef3d0b57144ca5a147a893570d8683
Source dataset
uspto-grants-1998_12
Patent number
US05852023

Reaction notes

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