Thionyl Chloride → 2-(5-Bromo-2-fluorophenyl)-4-Chloropteridine

HRID 928264

Reaction equation

HRID 928264 reaction equation
S(Cl)([Cl:3])=O.[Br:5][C:6]1[CH:7]=[CH:8][C:9]([F:23])=[C:10]([C:12]2[NH:21][C:20](=O)[C:19]3[C:14](=[N:15][CH:16]=[CH:17][N:18]=3)[N:13]=2)[CH:11]=1>C(Cl)(Cl)Cl.CN(C=O)C>[Br:5][C:6]1[CH:7]=[CH:8][C:9]([F:23])=[C:10]([C:12]2[N:21]=[C:20]([Cl:3])[C:19]3[C:14](=[N:15][CH:16]=[CH:17][N:18]=3)[N:13]=2)[CH:11]=1

Participants

5

Reactant 2

HCID 24386Thionyl ChlorideHCID 1361099582-(5-Bromo-2-fluoro-phenyl)-3H-pteridin-4-one

Product 1

HCID 577423812-(5-Bromo-2-fluorophenyl)-4-ChloropteridineYield 99.3%

Reagents, catalysts & solvents 2

HCID 6212ChloroformSolventHCID 6228DimethylformamideSolvent

Procedure

Thionyl chloride (371 mg, 3.11 mmol) was added to the stirred suspension of 2-(5-bromo-2-fluorophenyl)pteridin-4-one 104 (200 mg, 0.623 mmol) in chloroform (5 mL) and dry DMF (100 μL). The reaction mixture was refluxed under nitrogen for 1 h (starting material gone by HPLC). The solvent was removed in vacuo. Then the residue was triturated in Et2O and filtered off to give 210 mg of the title product 106 as a yellow solid (LCMS analysis).

Workup

  1. temperatureThe reaction mixture was refluxed under nitrogen for 1 h (starting material gone by HPLC)
  2. customThe solvent was removed in vacuo
  3. customThen the residue was triturated in Et2O
  4. filtrationfiltered off

Sources & evidence

ORD record
ord-66c332a926ac4642aa5cca4f7bd70f04
Source dataset
uspto-grants-2016_03
Patent number
US09290502B2

Linked notes

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