Dimethylformamide → HCID 22599797, compound

HRID 1592176Notes

Reaction equation

HRID 1592176 reaction equation
[CH2:1]([O:5][C:6]1[CH:11]=[C:10]([NH:12][CH2:13][CH3:14])[N:9]=[CH:8][N:7]=1)[C:2]#[C:3][CH3:4].[CH2:15](Cl)[CH:16]=C.[H-].[Na+].[CH3:21]N(C)C=O>>[CH2:1]([O:5][C:6]1[CH:11]=[C:10]([N:12]([CH2:15][CH3:16])[CH2:13][CH:14]=[CH2:21])[N:9]=[CH:8][N:7]=1)[C:2]#[C:3][CH3:4]

Participants

5

Reactant 4

HCID 6228DimethylformamideHCID 7850Allyl chlorideHCID 24758Sodium hydrideHCID 22599788HCID 22599788, compound

Product 1

HCID 22599797HCID 22599797, compound

Procedure

In 2 ml of N,N-dimethylformamide were dissolved 153 mg of 4-(2-butynyloxy)-6-(ethylamino)pyrimidine and 67 mg of allyl chloride, to which 40 mg of sodium hydride (60% in oil) was added, followed by stirring at room temperature for 3 hours. Then, ice water was added to the reaction mixture, which was extracted with ethyl acetate. The organic layer was washed twice with an aqueous sodium chloride solution, dried over anhydrous magnesium sulfate, and then concentrated. The residue was subjected to preparative silica gel thin layer chromatography to give 157 mg of 4-(2-butynyloxy)-6-(N-ethyl-N-allylamino)pyrimidine (the present compound (110)).

Workup

  1. extractionwas extracted with ethyl acetate
  2. washThe organic layer was washed twice with an aqueous sodium chloride solution
  3. dry with materialdried over anhydrous magnesium sulfate
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-e8b40c6b9b664d80822bd5aa937d895a
Source dataset
uspto-grants-2007_11
Patent number
US07291730B2

Reaction notes

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