Cornforth reagent → N-[4-(4-fluorophenyl)-5-[(E)-3-oxoprop-1-enyl]-6-propan-2-ylpyrimidin-2-yl]-N-methylmethanesulfonamide

HRID 1881708Notes

Reaction equation

HRID 1881708 reaction equation
C/[C:2](/[OH:27])=[CH:3]\[CH2:4][C:5]1[C:6]([C:20]2[CH:25]=[CH:24][C:23]([F:26])=[CH:22][CH:21]=2)=[N:7][C:8]([N:14]([CH3:19])[S:15]([CH3:18])(=[O:17])=[O:16])=[N:9][C:10]=1[CH:11]([CH3:13])[CH3:12].[Cr](O[Cr]([O-])(=O)=O)([O-])(=O)=O.[NH+]1C=CC=CC=1.[NH+]1C=CC=CC=1>ClCCl>[F:26][C:23]1[CH:22]=[CH:21][C:20]([C:6]2[C:5](/[CH:4]=[CH:3]/[CH:2]=[O:27])=[C:10]([CH:11]([CH3:13])[CH3:12])[N:9]=[C:8]([N:14]([CH3:19])[S:15]([CH3:18])(=[O:17])=[O:16])[N:7]=2)=[CH:25][CH:24]=1

Participants

4

Reactant 2

HCID 2724130Cornforth reagentHCID 86639490HCID 86639490, compound

Product 1

HCID 11574390N-[4-(4-fluorophenyl)-5-[(E)-3-oxoprop-1-enyl]-6-propan-2-ylpyrimidin-2-yl]-N-methylmethanesulfonamide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

Methyl (2E)-3-[4-(4-fluorophenyl)-6-isopropyl-2-(N-methyl-N-methylsulfonyl-amino)pyrimidin-5-yl]propen-1-ol (5.1 g) was added to molecular sieves (1 g) in dichloromethane (50 ml) and stirred for 15 min at room temperature. A solution of pyridinium dichromate (6.07 g) in dichloromethane (20 ml) was added to the above reaction mixture and continued stirring for 5 h at room temperature. After completion of the reaction, the reaction mass was filtered through a column of silica gel (230-400 mesh) and the eluate was distilled under reduced pressure to yield a semi-solid compound, which was crystallized from Hexane : Ethyl acetate (95 : 5 v/v) to yield (2E)-3-[4-(4-fluorophenyl)-6-isopropyl-2-(N-methyl-N-methylsulfonylamino)pyrimidin-5-yl]-propenal.

Workup

  1. stirringcontinued stirring for 5 h at room temperature
  2. customAfter completion of the reaction
  3. filtrationthe reaction mass was filtered through a column of silica gel (230-400 mesh)
  4. distillationthe eluate was distilled under reduced pressure
  5. customto yield a semi-solid compound, which
  6. customwas crystallized from Hexane : Ethyl acetate (95 : 5 v/v)

Sources & evidence

ORD record
ord-b4b5e1752bde486e994a9cc75bfbd4e9
Source dataset
uspto-grants-2012_11
Patent number
US08318933B2

Reaction notes

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