Potassium Carbonate → HCID 18613742, compound

HRID 705114Notes

Reaction equation

HRID 705114 reaction equation
[CH2:1]([C:3]1[N:8]([C:9]2[CH:14]=[CH:13][C:12]([F:15])=[CH:11][CH:10]=2)[C:7](=[O:16])[CH:6]=[CH:5][N:4]=1)[CH3:2].C([O-])(=O)C.[Na+].[Br:22]Br.C(=O)([O-])[O-].[K+].[K+]>C(O)(=O)C.O>[Br:22][CH:1]([C:3]1[N:8]([C:9]2[CH:14]=[CH:13][C:12]([F:15])=[CH:11][CH:10]=2)[C:7](=[O:16])[CH:6]=[CH:5][N:4]=1)[CH3:2]

Participants

7

Reactant 4

HCID 11430Potassium CarbonateHCID 24408BromineHCID 517045Sodium AcetateHCID 18613749HCID 18613749, compound

Product 1

HCID 18613742HCID 18613742, compoundYield 96%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 962WaterSolvent

Procedure

A solution of the pyrimidinone (24) (150 mg, 0.69 mmol) and sodium acetate (140 mg) in glacial acetic acid (1.5 mL) was warmed to 40° C. and treated dropwise with a preformed bromine solution (0.7 mL bromine in 10 mL of glacial acetic acid) (0.55 mL, 0.69 mmol). After 2 h, water (20 mL) was added to the mixture which was subsequently basified with potassium carbonate, and extracted with dichloromethane (2×10 mL). The combined organic phases were washed with water (10 mL), dried (MgSO4), and concentrated to give the title bromide (25) (196 mg, 96%) as a pale brown oil:

Workup

  1. extractionextracted with dichloromethane (2×10 mL)
  2. washThe combined organic phases were washed with water (10 mL)
  3. dry with materialdried (MgSO4)
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-81e5dba4b9524d79bbb3987d03bd8c62
Source dataset
uspto-grants-2015_11
Patent number
US09173869B2

Reaction notes

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