O-Xylene → HCID 18182410, compound

HRID 1359299Notes

Reaction equation

HRID 1359299 reaction equation
[CH2:1]([C:8]1[C:13]([Br:14])=[CH:12][N:11]=[C:10](I)N=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[N:16]1[CH:21]=[CH:20][CH:19]=[C:18]([Sn](CCCC)(CCCC)CCCC)[CH:17]=1.[C:35]1(C)C(C)=CC=CC=1>>[CH2:1]([C:8]1[C:13]([Br:14])=[CH:12][N:11]=[C:10]([C:18]2[CH:17]=[N:16][CH:21]=[CH:20][CH:19]=2)[CH:35]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 3

HCID 7237O-XyleneHCID 34838483-(Tributylstannyl)pyridineHCID 18182364HCID 18182364, compound

Product 1

HCID 18182410HCID 18182410, compound

Procedure

A mixture of 440 mg of 4-benzyl-5-bromo-2-iodopyrimidine, 430 mg of (3-pyridyl)tributyltin, 68 mg of tetrakis (triphenylphosphine)palladium(0) and 5 ml of xylene was heated under ref lux for one hour in a nitrogen atmosphere. After cooling as it was, silica gel was added to the reaction solution and the solvent was removed. The residue was subjected to silica gel column chromatography using 30% ethyl acetate/hexane, to give 110 mg of the target compound.

Workup

  1. temperaturewas heated under ref lux for one hour in a nitrogen atmosphere
  2. temperatureAfter cooling as it
  3. additionsilica gel was added to the reaction solution
  4. customthe solvent was removed

Sources & evidence

ORD record
ord-bf2d86c431334814823b9bed89ffef8b
Source dataset
uspto-grants-2003_07
Patent number
US06599917B1

Reaction notes

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