Lithium iodide → HCID 9862341, compound

HRID 1611256Notes

Reaction equation

HRID 1611256 reaction equation
[CH2:1]([C:3]1[C:4](=[O:19])[NH:5][C:6](=[O:18])[NH:7][C:8]=1[S:9][C:10]1[CH:15]=[C:14]([CH3:16])[CH:13]=[C:12]([CH3:17])[CH:11]=1)[CH3:2].Br[CH2:21][CH:22]1[CH2:24][CH2:23]1.C(=O)(O)[O-].[Na+].[I-].[Li+]>CN(C)C=O>[CH:22]1([CH2:21][N:7]2[C:8]([S:9][C:10]3[CH:11]=[C:12]([CH3:17])[CH:13]=[C:14]([CH3:16])[CH:15]=3)=[C:3]([CH2:1][CH3:2])[C:4](=[O:19])[NH:5][C:6]2=[O:18])[CH2:24][CH2:23]1

Participants

6

Reactant 4

HCID 66321Lithium iodideHCID 81503BromomethylcyclopropaneHCID 516892Sodium BicarbonateHCID 104927276-(3,5-dimethylphenyl)sulfanyl-5-ethyl-1H-pyrimidine-2,4-dione

Product 1

HCID 9862341HCID 9862341, compoundYield 46%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
90 °C

Procedure

To a solution of 5-ethyl-6-(3,5-dimethylphenyl)thio-2,4-pyrimidinedione 276 mg, 1.0 mmol) and bromomethyl cyclopropane (160 mg, 1.0 mmol, 85%) dissolved in dimethylformamide (5 ml), sodium bicarbonate (126 mg, 1.50 mmol) and lithium iodide (13.0 mg, 0.10 mmol) were added. The resulting mixture was stirred at 90° C. for 24 hrs, distilled under the reduced pressure to remove dimethylformamide and purified with column chromatography to obtain the titled compound as a white solid (152 mg, yield: 46.0%).

Workup

  1. distillationdistilled under the reduced pressure
  2. customto remove dimethylformamide
  3. custompurified with column chromatography

Sources & evidence

ORD record
ord-c44327e310684504bb7c9c656360c55f
Source dataset
uspto-grants-2006_01
Patent number
US06987114B1

Reaction notes

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