Thionyl Chloride → HCID 86677018, compound

HRID 2401164Notes

Reaction equation

HRID 2401164 reaction equation
[Br:1][C:2]1[C:3](=O)[NH:4][C:5]([N:13]2[CH:17]=[CH:16][CH:15]=[N:14]2)=[N:6][C:7]=1[N:8]1[CH:12]=[CH:11][CH:10]=[N:9]1.S(Cl)([Cl:21])=O>CN(C=O)C.C(Cl)Cl>[Br:1][C:2]1[C:3]([Cl:21])=[N:4][C:5]([N:13]2[CH:17]=[CH:16][CH:15]=[N:14]2)=[N:6][C:7]=1[N:8]1[CH:12]=[CH:11][CH:10]=[N:9]1

Participants

5

Reactant 2

HCID 24386Thionyl ChlorideHCID 136333995HCID 136333995, compound2×

Product 1

HCID 86677018HCID 86677018, compoundYield 61.5%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent2×

Procedure

To a solution of 1 g (3.26 mmol) of 5-bromo-2,6-di(1H-pyrazol-1-yl)pyrimidin-4(3H)-one (intermediate 8) in 10 ml of DMF and 40 ml of DCM was added dropwise a solution of 0.71 ml (9.8 mmol) of thionyl chloride in 10 ml DCM. The reaction mixture was refluxed for two hours, at which time no starting material was observed by TLC. The solution was extracted two times with 10 ml of saturated solution of NaHCO3 and Brine. The organic layer was separated, dried with MgSO4 and concentrated to give 0.65 g (61.5%) of the 4-chloro-pyrimidine derivative.

Workup

  1. temperatureThe reaction mixture was refluxed for two hours, at which time no starting material
  2. extractionThe solution was extracted two times with 10 ml of saturated solution of NaHCO3 and Brine
  3. customThe organic layer was separated
  4. dry with materialdried with MgSO4
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-3645f257f1b44aeb81ceab873ddb5563
Source dataset
uspto-grants-2014_08
Patent number
US08796284B2

Reaction notes

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