Tetrahydrofuran → [5-Ethyl-6-(furan-2-yl)-pyrimidin-4-yl]-hydrazine

HRID 1527641Notes

Reaction equation

HRID 1527641 reaction equation
Cl[C:2]1[C:7]([CH2:8][CH3:9])=[C:6]([C:10]2[O:11][CH:12]=[CH:13][CH:14]=2)[N:5]=[CH:4][N:3]=1.O.[NH2:16][NH2:17].C(N(CC)CC)C.C1COCC1>O>[CH2:8]([C:7]1[C:2]([NH:16][NH2:17])=[N:3][CH:4]=[N:5][C:6]=1[C:10]1[O:11][CH:12]=[CH:13][CH:14]=1)[CH3:9]

Participants

6

Reactant 4

HCID 8028TetrahydrofuranHCID 8471TriethylamineHCID 24654Hydrazine hydrate (1:1)2×HCID 656454164-Chloro-5-ethyl-6-(furan-2-yl)-pyrimidine

Product 1

HCID 67814467[5-Ethyl-6-(furan-2-yl)-pyrimidin-4-yl]-hydrazineYield 97.1%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 4-chloro-5-ethyl-6-(furan-2-yl)-pyrimidine (3.0 g), hydrazine monohydrate (3.0 g), triethylamine (3.0 g), and THF (20 ml) was stirred under reflux for 2 hours. To the mixture, hydrazine monohydrate (1 g) was added, and stirred under reflux for 3 hours. After standing to cool the reaction mixture to room temperature, to the reaction mixture, water was added, and extracted with ethyl acetate. The organic layer was dried over sodium sulfate, and concentrated under reduced pressure to give 2.85 g of [5-ethyl-6-(furan-2-yl)-pyrimidin-4-yl]-hydrazine.

Workup

  1. temperatureunder reflux for 2 hours
  2. stirringstirred
  3. temperatureunder reflux for 3 hours
  4. extractionextracted with ethyl acetate
  5. dry with materialThe organic layer was dried over sodium sulfate
  6. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-19306e042661451f8b644e57485b585c
Source dataset
uspto-grants-2015_07
Patent number
US09089136B2

Reaction notes

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