4-Chlorobenzenesulfonyl chloride → HCID 66972133, compound

HRID 1469116Notes

Reaction equation

HRID 1469116 reaction equation
[NH2:1][C:2]1[C:7]([F:8])=[CH:6][N:5]=[C:4]([OH:9])[N:3]=1.[Cl:10][C:11]1[CH:16]=[CH:15][C:14]([S:17](Cl)(=[O:19])=[O:18])=[CH:13][CH:12]=1>C(#N)C>[NH2:1][C:2]1[C:7]([F:8])=[CH:6][N:5]([S:17]([C:14]2[CH:15]=[CH:16][C:11]([Cl:10])=[CH:12][CH:13]=2)(=[O:19])=[O:18])[C:4](=[O:9])[N:3]=1

Participants

4

Reactant 2

HCID 73984-Chlorobenzenesulfonyl chlorideHCID 178509007HCID 178509007, compound

Product 1

HCID 66972133HCID 66972133, compoundYield 41%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
70 °C

Procedure

To 4-amino-5-fluoro-pyrimidin-2-ol* (1.0 g, 7.75 mmol) in acetonitrile (CH3CN; 40 mL) was added bis-N,O-trimethylsilylacetamide (BSA; 5.7 mL, 23.3 mmol) and the mixture was heated to 70° C. for 1 h resulting in a clear solution. After cooling to room temperature, 4-chlorobenzene sulfonyl chloride (1.8 g, 8.5 mmol) was added, and the mixture was stirred for 24 h. The solvent was evaporated and the residue was partitioned between EtOAc and brine. The organic phase was dried over MgSO4, filtered, and evaporated to yield the crude product as a white solid (1.3 g). Recrystallization from EtOAc and heptane furnished the title product as a white solid (0.96 g, 41%): mp 174-178° C.; 1H NMR (300 MHz, CDCl3) δ 8.5 (br s, 1H), 8.08 (d, J=5.9 Hz, 1H), 8.04-7.98 (m, 2H), 7.55-7.49 (m, 2H), 5.9 (br s, 1H); ESIMS m/z 304 ([M+H]+).

Workup

  1. customresulting in a clear solution
  2. temperatureAfter cooling to room temperature
  3. customThe solvent was evaporated
  4. customthe residue was partitioned between EtOAc and brine
  5. dry with materialThe organic phase was dried over MgSO4
  6. filtrationfiltered
  7. customevaporated
  8. customto yield the crude product as a white solid (1.3 g)
  9. customRecrystallization from EtOAc and heptane

Sources & evidence

ORD record
ord-647829de3b4d4347bd98d137e15e2f44
Source dataset
uspto-grants-2015_04
Patent number
US09006259B2

Reaction notes

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