Toluene → HCID 131723109, compound

HRID 1698784Notes

Reaction equation

HRID 1698784 reaction equation
[Br:1][C:2]1[C:3](=[O:9])[NH:4][C:5](=[O:8])[NH:6][CH:7]=1.[I-].[Na+].C(=O)([O-])[O-].[K+].[K+].[CH2:18](Br)[C:19]#[CH:20].[C:22]1(C)[CH:27]=CC=C[CH:23]=1>O.CN(C=O)C>[CH2:18]([C:7]1[NH:6][C:5](=[O:8])[N:4]([CH2:27][C:22]#[CH:23])[C:3](=[O:9])[C:2]=1[Br:1])[C:19]#[CH:20]

Participants

8

Reactant 5

HCID 1140TolueneHCID 5238Sodium IodideHCID 58025-BromouracilHCID 7842Propargyl bromideHCID 11430Potassium Carbonate

Product 1

HCID 131723109HCID 131723109, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

5 g of 5-bromouracil (26.18 mmole) available from Aldrich Chemical Co., 0.196 g of sodium iodide (1.31 mmole), and 35 mL of DMF were added to a 200 mL two-necked round bottomed flask. The mixture was stirred for 10 minutes. 5.065 g of potassium carbonate (36.65 mmole) was added to the mixture. Then 8.3687 g of 80% propargyl bromide available from Aldrich Chemical Co. in toluene was added dropwise over 1.5 hours. The mixture was stirred at room temperature for 16 hours to yield a milky solution. The solution was added to a separatory funnel with 200 mL of deionized water and extracted twice with 100 mL portions of 1,2-dichloromethane. The organic layers were combined and dried over magnesium sulfate. The mixture was filtered to remove any solids and evaporated under vacuum to obtain a low volume liquid. The liquid was placed on a Kugelrohr apparatus to remove any DMF in the liquid to yield 1N,3N-bis(2-propynyl)-5-bromouracil as a solid which was approximately 98% pure as determined by HPLC.

Workup

  1. stirringThe mixture was stirred at room temperature for 16 hours
  2. customto yield a milky solution
  3. extractionextracted twice with 100 mL portions of 1,2-dichloromethane
  4. dry with materialdried over magnesium sulfate
  5. filtrationThe mixture was filtered
  6. customto remove any solids
  7. customevaporated under vacuum
  8. customto obtain a low volume liquid
  9. customto remove any DMF in the liquid

Sources & evidence

ORD record
ord-e9ada24ee19b40c3a8e2d23cd6c49836
Source dataset
uspto-grants-2002_02
Patent number
US06344460B1

Reaction notes

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