1,4-Dibromobutane → HCID 19766728, compound

HRID 359400Notes

Reaction equation

HRID 359400 reaction equation
[H-].[Na+].[CH3:3][C:4]1[S:13][C:7]2[N:8]=[CH:9][NH:10][C:11](=[O:12])[C:6]=2[CH:5]=1.[Br:14][CH2:15][CH2:16][CH2:17][CH2:18]Br>CN(C=O)C>[Br:14][CH2:15][CH2:16][CH2:17][CH2:18][N:8]1[C:7]2[S:13][C:4]([CH3:3])=[CH:5][C:6]=2[C:11](=[O:12])[NH:10][CH2:9]1

Participants

5

Reactant 3

HCID 80561,4-DibromobutaneHCID 24758Sodium hydrideHCID 7350186-Methyl-3H-thieno[2,3-d]pyrimidin-4-one

Product 1

HCID 19766728HCID 19766728, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a stirring mixture of NaH (1.7 g, 0.072 mol) in 150 ml anhydrous DMF at room temperature was added 4.0 g (0.024 mol) of 6-methyl thieno[2,3-d]pyrimidin-4(3H)-one (IV-3) and, after the cessation of gas evolution, 20.7 g (0.96 mol) of 1,4-dibromobutane was added. Reaction was complete after 4 days. The solution was concentrated in vacuo, the residue partitioned between CH2Cl2 and water, and the organic phase isolated, dried (MgSO4), and filtered. The filtrate was concentrated and excess dibromobutane removed by Kugelrohr distillation. The solid product residue weighed 4.12 g (57%). The NMR was consistent with the assigned structure.

Workup

  1. customReaction
  2. concentrationThe solution was concentrated in vacuo
  3. customthe residue partitioned between CH2Cl2 and water
  4. customthe organic phase isolated
  5. dry with materialdried (MgSO4)
  6. filtrationfiltered
  7. concentrationThe filtrate was concentrated
  8. customexcess dibromobutane removed by Kugelrohr distillation

Sources & evidence

ORD record
ord-562a982465744cb78fe6d5fdbcfba70a
Source dataset
uspto-grants-1991_03
Patent number
US05001130

Reaction notes

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