Ethanol → 4,6-Dimethoxy-2-(4-trifluoromethyl-thiazol-2-yl)-pyrimidin-4-ol

HRID 880807Notes

Reaction equation

HRID 880807 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[C:7]([O:9][CH3:10])[N:6]=[C:5]([C:11](=[S:13])[NH2:12])[N:4]=1.Br[CH2:15][C:16](=O)[C:17]([F:20])([F:19])[F:18].CC[OH:24]>>[CH3:10][O:9][C:7]1([OH:24])[CH:8]=[C:3]([O:2][CH3:1])[N:4]=[C:5]([C:11]2[S:13][CH:15]=[C:16]([C:17]([F:20])([F:19])[F:18])[N:12]=2)[NH:6]1

Participants

4

Reactant 3

HCID 702EthanolHCID 790083-Bromo-1,1,1-trifluoro-2-propanoneHCID 582827014,6-Dimethoxy-pyrimidin-2-carbothioic acid amide

Product 1

HCID 1784935964,6-Dimethoxy-2-(4-trifluoromethyl-thiazol-2-yl)-pyrimidin-4-olYield 12%

Conditions

Temperature
90 °C

Procedure

To a solution of compound 287 (14 g, 1 eq.) in EtOH (140 mL) was added 3-bromo-1,1,1-trifluoroacetone (8.8 mL, 1.2 eq.). The mixture was stirred at 90° C. for 16 hrs and concentrated in vacuo. DCM (20 mL) and water (20 mL) were added. Organics were dried over Na2SO4, filtered, concentrated under reduced pressure, and flushed on a silica gel column with 5% MeOH/DCM to yield compound 288 as a beige compound in 12% yield. MS (ESI, EI+): m/z=292 (MH+).

Workup

  1. concentrationconcentrated in vacuo
  2. additionDCM (20 mL) and water (20 mL) were added
  3. dry with materialOrganics were dried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure
  6. customflushed on a silica gel column with 5% MeOH/DCM

Sources & evidence

ORD record
ord-df69b62e36d241ddb6a046909ed2a37c
Source dataset
uspto-grants-2015_03
Patent number
US08993595B2

Reaction notes

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