Ethanol → HCID 18328938, compound

HRID 1249731Notes

Reaction equation

HRID 1249731 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][N:11]([CH2:14][CH:15]2[CH2:20][CH2:19][N:18]([C:21](OCC3C=CC=CC=3)=O)[CH2:17][CH2:16]2)[C:10](=[O:31])[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[CH2:32](O)C.[H][H].Cl[C:38]1[N:43]=[C:42]([Cl:44])[CH:41]=C(C)[N:39]=1>[Pd].C(N(CC)CC)C>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][N:11]([CH2:14][CH:15]2[CH2:16][CH2:17][N:18]([C:21]3[CH:41]=[C:42]([Cl:44])[N:43]=[C:38]([CH3:32])[N:39]=3)[CH2:19][CH2:20]2)[C:10](=[O:31])[CH2:9]1)=[O:7])([CH3:3])([CH3:2])[CH3:4]

Participants

7

Reactant 4

HCID 702Ethanol2×HCID 794712,4-Dichloro-6-methylpyrimidineHCID 54050102HCID 54050102, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 18328938HCID 18328938, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8471TriethylamineSolvent

Procedure

To a mixture of 1-tert-butyloxycarbonyl-3-oxo-4-[1-(benzyloxycarbonyl)-4-piperidylmethyl]piperazine (1.35 g), palladium on charcoal (10% w/w, 0.1 g) and ethanol (20 ml) was agitated under an atmosphere of hydrogen at 25° C. for 2 hours until hydrogen uptake was complete. The mixture was filtered and the filtrate was evaporated to give an oil which was mixed with 2,4-dichloro-6-methylpyrimidine(502 mg), ethanol (20 ml) and triethylamine (0.86 ml), heated to reflux for 18 hours. The cooled mixture was evaporated then diluted with dichloromethane and washed with water, dried (Na2SO4) then filtered onto a silica column (10 g Bond Elut) eluting with 0-5% methanol in dichloromethane to give 1-tert-butyloxycarbonyl-3-oxo-4-[1-(2-methyl-6-chloropyrimidin-4-yl )-4piperidylmethyl]piperazine (1.01 g).

Workup

  1. filtrationThe mixture was filtered
  2. customthe filtrate was evaporated
  3. customto give an oil which
  4. temperatureheated
  5. temperatureto reflux for 18 hours
  6. customThe cooled mixture was evaporated
  7. additionthen diluted with dichloromethane
  8. washwashed with water
  9. dry with materialdried (Na2SO4)
  10. filtrationthen filtered onto a silica column (10 g Bond Elut)
  11. washeluting with 0-5% methanol in dichloromethane

Sources & evidence

ORD record
ord-357cf7396f6440ac92fba2429523ea1b
Source dataset
uspto-grants-2002_01
Patent number
US06335341B1

Reaction notes

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