4-Chloro-2-methylthiopyrimidine → HCID 67253399, compound

HRID 2042045Notes

Reaction equation

HRID 2042045 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([OH:9])[CH:5]=[CH:6][C:7]=1[F:8].CC(C)([O-])C.[K+].Cl[C:17]1[CH:22]=[CH:21][N:20]=[C:19]([S:23][CH3:24])[N:18]=1>CC(N(C)C)=O.O>[F:8][C:7]1[CH:6]=[CH:5][C:4]([O:9][C:17]2[CH:22]=[CH:21][N:20]=[C:19]([S:23][CH3:24])[N:18]=2)=[CH:3][C:2]=1[NH2:1]

Participants

6

Reactant 3

HCID 971134-Chloro-2-methylthiopyrimidineHCID 135191803-Amino-4-fluorophenolHCID 23665647Potassium tert-butoxide

Product 1

HCID 67253399HCID 67253399, compoundYield 85.2%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 31374DimethylacetamideSolvent

Conditions

Temperature
50 °C

Procedure

In DMA (10 mL) was placed 3-amino-4-fluorophenol (500 mg, 3.93 mmol), potassium t-butoxide (441 mg, 3.93 mmol) and 4-chloro-2-(methylthio)pyrimidine (632 mg, 3.93 mmol). The mixture was warmed to 50° C. and stirred overnight. The mixture was cooled to RT and diluted with water (30 mL), extracted with ethyl acetate (2×25 mL) and the combined organic phases washed with brine, dried (Na2SO4) and concentrated to yield a dark oil. The oil was purified by column chromatography to yield 2-fluoro-5-(2-(methylthio)pyrimidin-4-yloxy)benzenamine (841 mg, 85% yield) as an oil which was used without further purification. MS (ESI) m/z: 252.0 (M+H+).

Workup

  1. temperatureThe mixture was cooled to RT
  2. extractionextracted with ethyl acetate (2×25 mL)
  3. washthe combined organic phases washed with brine
  4. dry with materialdried (Na2SO4)
  5. concentrationconcentrated
  6. customto yield a dark oil
  7. customThe oil was purified by column chromatography

Sources & evidence

ORD record
ord-c8e8c58df32747f8b6892278ec21e420
Source dataset
uspto-grants-2013_11
Patent number
US08586565B2

Reaction notes

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