Triethylamine → HCID 53936376, compound

HRID 1492963Notes

Reaction equation

HRID 1492963 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-2092d67b42f24b5787596e0efe736005
Source dataset
uspto-grants-1994_12
Patent number
US05376685

Reaction notes

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