N-bromobutanimide → HCID 21183872, compound

HRID 1384850Notes

Reaction equation

HRID 1384850 reaction equation
[CH3:1][S:2][C:3]1[N:4]([CH2:13][CH2:14][CH3:15])[C:5](=[O:12])[C:6]2[S:11][CH:10]=[CH:9][C:7]=2[N:8]=1.C([N-]C(C)C)(C)C.[Li+].[Br:24]N1C(=O)CCC1=O>O1CCCC1>[Br:24][C:10]1[S:11][C:6]2[C:5](=[O:12])[N:4]([CH2:13][CH2:14][CH3:15])[C:3]([S:2][CH3:1])=[N:8][C:7]=2[CH:9]=1

Participants

5

Reactant 3

HCID 67184N-bromobutanimideHCID 2724682Lithium diisopropylamideHCID 211838812-(Methylthio)-3-propylthieno[3,2-d]pyrimidin-4(3H)-one

Product 1

HCID 21183872HCID 21183872, compoundYield 29.8%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent3×

Conditions

Temperature
-78 °C

Procedure

In a sulfonation flask, 9.6 g (0.04 mol) of 2-methylsulfanyl-3-propyl-3H-thieno[3.2-d]-pyrimidin-4-one are added to 200 ml of absolute tetrahydrofuran. Subsequently, 4.07 g (0.042 mol) of lithium diisopropylamide, dissolved in 50 ml of absolute tetrahydrofuran, are added dropwise under N2 such that the internal temperature remains constant at about −78° C. The mixture is stirred for 1 hour at −78° C. and then a solution of 8.5 g (0.048 mol) of N-bromosuccinimide in 40 ml of absolute tetrahydrofuran is added dropwise such that the internal temperature remains constant at about −78° C. The condenser is then removed and the mixture is slowly warmed to room temperature. The tetrahydrofuran is removed in a water-jet vacuum and the residue is dissolved in ethyl acetate. The organic phase is washed with water, dried over sodium sulfate and the ethyl acetate is then removed in the water-jet vacuum. The crude product is purified by column chromatography over silica gel (eluant: ethyl acetate/hexane=1:5), giving 3.8 g of 6-bromo-2-methylsulfanyl-3-propyl-3H-thieno[3.2-d]pyrimidin-4-one in the form of a yellow powder having a melting point of 138-141° C.

Workup

  1. additionare added dropwise under N2 such that the internal temperature
  2. customremains constant at about −78° C
  3. customremains constant at about −78° C
  4. customThe condenser is then removed
  5. temperaturethe mixture is slowly warmed to room temperature
  6. customThe tetrahydrofuran is removed in a water-jet vacuum
  7. dissolutionthe residue is dissolved in ethyl acetate
  8. washThe organic phase is washed with water
  9. dry with materialdried over sodium sulfate
  10. customthe ethyl acetate is then removed in the water-jet vacuum
  11. customThe crude product is purified by column chromatography over silica gel (eluant: ethyl acetate/hexane=1:5)

Sources & evidence

ORD record
ord-ab779a52a85f4a1eb940c1f9d63817f9
Source dataset
uspto-grants-2001_07
Patent number
US06262058B1

Reaction notes

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