Potassium Iodide → HCID 67051263, compound

HRID 1025004Notes

Reaction equation

HRID 1025004 reaction equation
[H-].[Na+].[F:3][C:4]1[C:9]([F:10])=[CH:8][CH:7]=[CH:6][C:5]=1[CH2:11][S:12][C:13]1[N:18]=[C:17]([NH:19][S:20]([N:23]2[CH2:26][CH2:25][CH2:24]2)(=[O:22])=[O:21])[CH:16]=[C:15]([O:27][CH3:28])[N:14]=1.ClC1C=C(OC)N=C(SCC2C=CC=C(F)C=2F)N=1.[CH3:48][O:49][C:50]1[CH:57]=[CH:56][C:53]([CH2:54]Cl)=[CH:52][CH:51]=1.[I-].[K+]>CN(C=O)C>[F:3][C:4]1[C:9]([F:10])=[CH:8][CH:7]=[CH:6][C:5]=1[CH2:11][S:12][C:13]1[N:18]=[C:17]([N:19]([CH2:54][C:53]2[CH:56]=[CH:57][C:50]([O:49][CH3:48])=[CH:51][CH:52]=2)[S:20]([N:23]2[CH2:24][CH2:25][CH2:26]2)(=[O:22])=[O:21])[CH:16]=[C:15]([O:27][CH3:28])[N:14]=1

Participants

7

Reactant 5

HCID 4875Potassium IodideHCID 24758Sodium hydrideHCID 699934-Methyloxybenzyl chlorideHCID 11516939HCID 11516939, compoundHCID 866198774-Chloro-2-([(2,3-difluorophenyl)methyl]thio]-6-methoxypyrimidine

Product 1

HCID 67051263HCID 67051263, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
0 °C

Procedure

60% Sodium hydride (0.42 g) was added to a solution of N-[2-[[(2,3-difluorophenyl)methyl]thio]-6-methoxypyrimidin-4-yl]azetidine-1-sulfonamide (the product of Example 35) (3.82 g) in anhydrous DMF (38 ml) stirred at 0° C. under nitrogen. The reaction mixture was stirred for a further 15 min when 4-methoxybenzylchloride (2.98 g) was added dropwise over one min followed by potassium iodide (1.66 g). After stirring at room temperature for 18 h. the reaction mixture was partitioned between EtOAc and H2O. The aqueous layer was separated and further extracted with EtOAc (2×). The combined organic extracts were washed with H2O, dried (MgSO4), filtered and the solvent evaporated under reduced pressure. The residue was purified by flash column chromatography on silica gel using EtOAc/iso-hexane (2:8) as eluent. The product was further purified by flash column chromatography on silica gel using DCM/isohexane (6:4) as eluent to give the subtitle product as a white solid. Yield: 2.4 g.

Workup

  1. additionwas added dropwise over one min
  2. stirringAfter stirring at room temperature for 18 h. the reaction mixture
  3. customwas partitioned between EtOAc and H2O
  4. customThe aqueous layer was separated
  5. extractionfurther extracted with EtOAc (2×)
  6. washThe combined organic extracts were washed with H2O
  7. dry with materialdried (MgSO4)
  8. filtrationfiltered
  9. customthe solvent evaporated under reduced pressure
  10. customThe residue was purified by flash column chromatography on silica gel
  11. customThe product was further purified by flash column chromatography on silica gel

Sources & evidence

ORD record
ord-7376c05c643c468f86ad812ceb0ae7f2
Source dataset
uspto-grants-2014_05
Patent number
US08722883B2

Reaction notes

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