Potassium Carbonate → HCID 69311856, compound

HRID 1947014Notes

Reaction equation

HRID 1947014 reaction equation
[F:1][C:2]1[CH:7]=[C:6]([OH:8])[CH:5]=[CH:4][C:3]=1[C:9]([C:11]1[CH:16]=[CH:15][N:14]=[C:13]([S:17][CH3:18])[N:12]=1)=[O:10].C([O-])([O-])=O.[K+].[K+].[CH3:25][S:26][CH2:27][CH2:28][CH2:29][CH2:30]S(C1C=CC(C)=CC=1)(=O)=O>CN1C(=O)CCC1>[F:1][C:2]1[CH:7]=[C:6]([O:8][CH2:30][CH2:29][CH2:28][CH2:27][S:26][CH3:25])[CH:5]=[CH:4][C:3]=1[C:9]([C:11]1[CH:16]=[CH:15][N:14]=[C:13]([S:17][CH3:18])[N:12]=1)=[O:10]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 69308467HCID 69308467, compoundHCID 69308635HCID 69308635, compound

Product 1

HCID 69311856HCID 69311856, compoundYield 73.5%

Reagents, catalysts & solvents 1

HCID 13387N-methyl-2-pyrrolidoneSolvent

Procedure

(2-Fluoro-4-hydroxyphenyl)-(2-methylsulfanyl-pyrimidin-4-yl)-methanone (2.26 g, 12.7 mmol), K2CO3 (3.5 g, 25.4 mmol) and 1-methylthio-4-tosylbutane (8.5 g, 44.5 mmol) were stirred in NMP for 1 h at 100° C., cooled to RT, filtered, diluted with water, and extracted into EtOAc. The combined organic layers were dried over sodium sulfate, filtered, concentrated in vacuo and purified by flash chromatography on a silica column eluting with hexane:ethyl acetate 9:1 to 3:2 to yield [2-fluoro-4-(4-methylsulfanyl-butoxy)-phenyl]-(2-methylsulfanyl-pyrimidin-4-yl)-methanone (3.42 g).

Workup

  1. filtrationfiltered
  2. additiondiluted with water
  3. extractionextracted into EtOAc
  4. dry with materialThe combined organic layers were dried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. custompurified by flash chromatography on a silica column
  8. washeluting with hexane:ethyl acetate 9:1 to 3:2

Sources & evidence

ORD record
ord-d383d155545149eda74f0dd6a3ee99c2
Source dataset
uspto-grants-2013_03
Patent number
US08399462B2

Reaction notes

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