Dimethylformamide → HCID 22599738, compound

HRID 1592175Notes

Reaction equation

HRID 1592175 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].Br[CH2:16][C:17]#CC.[H-].[Na+].CN(C)C=O.O1CC[CH2:29][CH2:28]1>>[CH2:1]([O:5][C:6]1[CH:11]=[C:10]([N:12]([CH2:28][CH3:29])[CH2:13][C:14]#[C:16][CH3:17])[N:9]=[CH:8][N:7]=1)[C:2]#[C:3][CH3:4]

Participants

6

Reactant 5

HCID 6228DimethylformamideHCID 8028TetrahydrofuranHCID 24758Sodium hydrideHCID 27568621-Bromo-2-butyneHCID 22599788HCID 22599788, compound

Product 1

HCID 22599738HCID 22599738, compound

Procedure

In 5 ml of tetrahydrofuran were dissolved 153 mg of 4-(2-butynyloxy)-6-(ethylamino)pyrimidine and 117 mg of 1-bromo-2-butyne, to which 40 mg of sodium hydride (60% in oil) was added, followed by stirring at room temperature for 7 hours. Then, 2 ml of N,N-dimethylformamide was further added, and the mixture was stirred 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 176 mg of 4-(2-butynyloxy)-6-(N-ethyl-N-(2-butynyl)amino)pyrimidine (the present compound (109)).

Workup

  1. stirringthe mixture was stirred at room temperature for 3 hours
  2. extractionwas extracted with ethyl acetate
  3. washThe organic layer was washed twice with an aqueous sodium chloride solution
  4. dry with materialdried over anhydrous magnesium sulfate
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-942d38b7fc9d45309ed34f5c62fef15e
Source dataset
uspto-grants-2007_11
Patent number
US07291730B2

Reaction notes

Loading…