Hydrochloric Acid → HCID 85927953, compound

HRID 729649Notes

Reaction equation

HRID 729649 reaction equation
[CH3:1][S:2]([NH2:5])(=[O:4])=[O:3].[H-].[Na+].[CH2:8]([S:15][C:16]1[N:21]=[C:20](Cl)[CH:19]=[C:18]([Cl:23])[N:17]=1)[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1.Cl>CN(C=O)C.CCOC(C)=O>[CH2:8]([S:15][C:16]1[N:21]=[C:20]([NH:5][S:2]([CH3:1])(=[O:4])=[O:3])[CH:19]=[C:18]([Cl:23])[N:17]=1)[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 24758Sodium hydrideHCID 72879MethanesulfonamideHCID 470488Pyrimidine, 4,6-dichloro-2-[(phenylmethyl)thio]-

Product 1

HCID 85927953HCID 85927953, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

To methane sulphonamide (1.47 g) in DMF (30 ml) was added 60% sodium hydride (0.59 g) at room temperature and stirred for 1 h. To this mixture was then added the subtitle product of step ii) and the mixture stirred at room temperature for 6 h. To the reaction mixture was added EtOAc (50 ml) and aqueous hydrochloric acid (50 ml, 1M). The organic layer was separated and washed with brine (20 ml), combined, dried (MgSO4) and evaporated to dryness under reduced pressure. The residue was purified by column chromatography (20 to 50% EtOAc/iso-hexane) to afford the subtitle compound as a yellow oil. Yield: 1.60 g.

Workup

  1. stirringstirred at room temperature for 6 h
  2. customThe organic layer was separated
  3. washwashed with brine (20 ml)
  4. dry with materialdried (MgSO4)
  5. customevaporated to dryness under reduced pressure
  6. customThe residue was purified by column chromatography (20 to 50% EtOAc/iso-hexane)

Sources & evidence

ORD record
ord-7a6241f770ec4ff08be0292ede4ea167
Source dataset
uspto-grants-2009_09
Patent number
US07582644B2

Reaction notes

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