Triethylamine → HCID 21477601, compound

HRID 1449711Notes

Reaction equation

HRID 1449711 reaction equation
[CH3:1][C:2]([CH3:23])([O:4][C:5]([N:7]1[CH2:12][CH2:11][N:10]([C:13]2[N:18]=[CH:17][N:16]=[C:15](Cl)[C:14]=2[N+:20]([O-])=O)[CH2:9][CH2:8]1)=[O:6])[CH3:3].C(N(CC)CC)C.[H][H]>[Pd].C(O)C>[CH3:3][C:2]([CH3:23])([O:4][C:5]([N:7]1[CH2:8][CH2:9][N:10]([C:13]2[N:18]=[CH:17][N:16]=[CH:15][C:14]=2[NH2:20])[CH2:11][CH2:12]1)=[O:6])[CH3:1]

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 21477639tert-Butyl 4-(6-chloro-5-nitropyrimidin-4-yl)piperazine-1-carboxylateHCID 178418361HCID 178418361, compound

Product 1

HCID 21477601HCID 21477601, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A mixture of 1-[1,1-dimethylethoxycarbonyl]-4-[4-chloro-5-nitro-6-pyrimidyl]piperazine and triethylamine (0.3 ml) and palladium on carbon (5%, 0.13 g) in ethanol (100 ml) is charged with hydrogen gas (30 psi). After the theoretical amount of hydrogen gas is consumed, the catalyst is removed under reduced pressure. The filtrate is concentrated under reduced pressure to a foam which is diluted with an aqueous saturated solution of potassium carbonate and dichloromethane. The phases are separated and the organic phase is dried over sodium sulfate and concentrated to give to give the title compound, NMR (CDCl3) 1.49, 3.49, 3.29, 3.56, 7.98, and 8.39 δ.

Workup

  1. customAfter the theoretical amount of hydrogen gas is consumed
  2. customthe catalyst is removed under reduced pressure
  3. concentrationThe filtrate is concentrated under reduced pressure to a foam which
  4. additionis diluted with an aqueous saturated solution of potassium carbonate and dichloromethane
  5. customThe phases are separated
  6. dry with materialthe organic phase is dried over sodium sulfate
  7. concentrationconcentrated
  8. customto give

Sources & evidence

ORD record
ord-cb1f54c5457446f089b0c5aad3a67df4
Source dataset
uspto-grants-1997_02
Patent number
US05599930

Reaction notes

Loading…