Pyrrolidine → (E)-5-(2-Methyl-4-nitro-5-(2-(pyrrolidin-1-yl)vinyl)phenoxy)pyrimidine

HRID 2361249Notes

Reaction equation

HRID 2361249 reaction equation
[CH3:1][C:2]1[CH:14]=[C:13]([N+:15]([O-:17])=[O:16])[C:12]([CH3:18])=[CH:11][C:3]=1[O:4][C:5]1[CH:6]=[N:7][CH:8]=[N:9][CH:10]=1.[NH:19]1[CH2:23][CH2:22][CH2:21][CH2:20]1.[CH3:24]N(C(OC)OC)C>CN(C=O)C>[CH3:1][C:2]1[CH:14]=[C:13]([N+:15]([O-:17])=[O:16])[C:12](/[CH:18]=[CH:24]/[N:19]2[CH2:23][CH2:22][CH2:21][CH2:20]2)=[CH:11][C:3]=1[O:4][C:5]1[CH:6]=[N:7][CH:8]=[N:9][CH:10]=1

Participants

5

Reactant 3

HCID 31268PyrrolidineHCID 78373Dimethylformamide dimethyl acetalHCID 679951355-(2,5-Dimethyl-4-nitrophenoxy)pyrimidine

Product 1

HCID 86681515(E)-5-(2-Methyl-4-nitro-5-(2-(pyrrolidin-1-yl)vinyl)phenoxy)pyrimidine

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of 5-(2,5-dimethyl-4-nitrophenoxy)pyrimidine (0.7243 g, 2.95 mmol), pyrrolidine (0.345 mL, 4.13 mmol) and DMF-DMA (0.551 mL, 4.13 mmol) in DMF (3.0 mL) under nitrogen was heated at 115° C. After 45 min, the reaction was cooled to room temperature and concentrated in vacuo, followed by a short-path distillation. The crude residue was used in the subsequent step.

Workup

  1. concentrationconcentrated in vacuo
  2. distillationfollowed by a short-path distillation

Sources & evidence

ORD record
ord-f5b426efe87a414f93ac4eae954b58d8
Source dataset
uspto-grants-2014_04
Patent number
US08685969B2

Reaction notes

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