Triethylamine → HCID 53936376, compound

HRID 892484Notes

Reaction equation

HRID 892484 reaction equation
C(N(CC)CC)C.Cl[C:9]1[N:14]=[C:13]([CH:15]=[CH:16][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[N:12]=[C:11]([CH3:23])[CH:10]=1.[H][H]>[Pd].CC([O-])=O.CC([O-])=O.[Pb+2].C(O)C>[CH3:23][C:11]1[CH:10]=[CH:9][N:14]=[C:13]([CH:15]=[CH:16][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[N:12]=1

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 53904091HCID 53904091, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 53936376HCID 53936376, compound

Reagents, catalysts & solvents 2

HCID 131709914Lindlars catalystCatalystHCID 702EthanolSolvent

Procedure

9.02 ml of triethylamine and 1.365 g of Lindlar catalyst are added to 13.65 g (59.17 mmol) of 6-chloro-4-methyl-2-(2-phenylethenyl)pyrimidine in 220 ml of absolute ethanol and hydrogenation is carried out at room temperature under normal pressure. When 1 equivalent of hydrogen has been absorbed, hydrogenation is terminated (after about 7.5 hours), and the reaction mixture is filtered with suction over Hyflo Super Cel® and concentrated in a rotary evaporator. Chromatography twice on silica gel with chloroform and then n-hexane/ethyl acetate 5-20% as eluants yields the pure title compound; m.p. 65°-67°.

Workup

  1. customis carried out at room temperature under normal pressure
  2. customhydrogenation is terminated (after about 7.5 hours)
  3. filtrationthe reaction mixture is filtered with suction over Hyflo Super Cel®
  4. concentrationconcentrated in a rotary evaporator

Sources & evidence

ORD record
ord-a42f09f8b4b14c8780e519f2dda29d14
Source dataset
uspto-grants-1992_06
Patent number
US05118709

Reaction notes

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