Water → HCID 18182304, compound

HRID 1359398Notes

Reaction equation

HRID 1359398 reaction equation
[H-].[Na+].[CH2:3]([C:10]1[C:15]([Br:16])=[CH:14][N:13]=[C:12](Cl)[N:11]=1)[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.[CH2:18]([OH:24])[C:19]1[O:23][CH:22]=[CH:21][CH:20]=1.O>C(OCC)C>[CH2:3]([C:10]1[C:15]([Br:16])=[CH:14][N:13]=[C:12]([O:24][CH2:18][C:19]2[O:23][CH:22]=[CH:21][CH:20]=2)[N:11]=1)[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1

Participants

6

Reactant 4

HCID 962WaterHCID 7361Furfuryl AlcoholHCID 24758Sodium hydrideHCID 18182475HCID 18182475, compound

Product 1

HCID 18182304HCID 18182304, compound

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Conditions

Temperature
90 °C

Procedure

14.1 mg of 60% oily sodium hydride was added to a mixture of 73.3 mg of 4-benzyl-5-bromo-2-chloropyrimidine (Production Example 15), 1 ml of furfuryl alcohol and 14.8 mg of cuprous iodide at room temperature, followed by stirring at 90° C. for 2 hours. Water and diethyl ether were added to the reaction solution, and the organic phase was washed with water and brine, dried over anhydrous magnesium sulfate and the solvent was removed. The residue was subjected to silica gel column chromatography using 10% ethyl acetate/hexane, to give 50.9 mg of the target compound.

Workup

  1. washthe organic phase was washed with water and brine
  2. dry with materialdried over anhydrous magnesium sulfate
  3. customthe solvent was removed

Sources & evidence

ORD record
ord-186927a5f3f640cb810079e76124280b
Source dataset
uspto-grants-2003_07
Patent number
US06599917B1

Reaction notes

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