Sodium hydride → HCID 22599740, compound

HRID 1759895Notes

Reaction equation

HRID 1759895 reaction equation
[CH2:1]([O:5][C:6]1[CH:11]=[C:10]([NH:12][CH:13]([CH3:15])[CH3:14])[N:9]=[CH:8][N:7]=1)[C:2]#[C:3][CH3:4].Br[CH2:17][C:18]#[C:19][CH3:20].[H-].[Na+]>O1CCCC1>[CH2:1]([O:5][C:6]1[CH:11]=[C:10]([N:12]([CH2:17][C:18]#[C:19][CH3:20])[CH:13]([CH3:15])[CH3:14])[N:9]=[CH:8][N:7]=1)[C:2]#[C:3][CH3:4]

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 27568621-Bromo-2-butyneHCID 22599864HCID 22599864, compound

Product 1

HCID 22599740HCID 22599740, compoundYield 75.6%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

In 5 ml of tetrahydrofuran were dissolved 164 mg of 4-(2-butynyloxy)-6-(isopropylamino)pyrimidine and 106 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 6 hours. Then, ice water was added to the reaction mixture, which was extracted with ethyl acetate. The organic layer was washed 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 155 mg of 4-(2-butynyloxy)-6-(N-(2-butynyl)-N-isopropylamino)pyrimidine (the present compound (107)).

Workup

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

Sources & evidence

ORD record
ord-aa62ebe898d1485599a5465c0949f248
Source dataset
uspto-grants-2005_01
Patent number
US06838463B2

Reaction notes

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