Bromine → HCID 178437802, compound

HRID 630299Notes

Reaction equation

HRID 630299 reaction equation
[CH2:1]([C:3]1[N:4]=[CH:5][S:6][C:7]=1[CH2:8][S:9][C:10]1[N:15]=[C:14]([OH:16])[CH:13]=[C:12]([C:17]([F:20])([F:19])[F:18])[N:11]=1)[CH3:2].C(Cl)(Cl)(Cl)Cl.C(Cl)Cl.[Br:29]Br.S([O-])([O-])(=O)=S.[Na+].[Na+]>C(Cl)Cl.O>[Br:29][C:13]1[C:14]([OH:16])=[N:15][C:10]([S:9][CH2:8][C:7]2[S:6][CH:5]=[N:4][C:3]=2[CH2:1][CH3:2])=[N:11][C:12]=1[C:17]([F:20])([F:19])[F:18]

Participants

7

Reactant 4

HCID 24408BromineHCID 24477Sodium ThiosulfateHCID 22996148Carbon tetrachloride methylene chlorideHCID 178437804HCID 178437804, compound

Product 1

HCID 178437802HCID 178437802, compoundYield 12%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

To a solution of 2-{[(4-ethyl-1,3-thiazol-5-yl)methyl]sulfanyl}-6-(trifluoromethyl)pyrimidin-4-ol (500 mg, 1.56 mmol) in a mixture of 2:1 CCl4-DCM (40 mL) was dropwise added bromine (80 μL, 1.56 mmol) at 0° C. After 1 hour of stirring at room temperature, water and a solution of sodium thiosulfate were added. The mixture was extracted with DCM (3 times). The combined organic phases were washed with brine, dried over magnesium sulfate, and evaporated to afford a crude oil. The residue was dissolved in DCM and purified on silica gel using DCM/MeOH (0 to 15%) to provide 5-bromo-2-{[(4-ethyl-1,3-thiazol-5-yl)methyl]sulfanyl}-6-(trifluoromethyl)pyrimidin-4-ol as a white solid (72 mg, 12% yield). 1H NMR (500 MHz, DMSO-d6): δ 1.17 (t, J=7.4 Hz, 3H), 2.75 (q, J=7.4 Hz, 2H), 4.64 (s, 2H), 8.87 (s, 1H). LRMS (ES′) m/z 402 (50%, M+2), 400 (50%, M).

Workup

  1. customat 0° C
  2. extractionThe mixture was extracted with DCM (3 times)
  3. washThe combined organic phases were washed with brine
  4. dry with materialdried over magnesium sulfate
  5. customevaporated
  6. customto afford a crude oil
  7. custompurified on silica gel

Sources & evidence

ORD record
ord-59aecc3d917c43b3be60fb0a6ab6336e
Source dataset
uspto-grants-2016_04
Patent number
US09315521B2

Reaction notes

Loading…