Benzenesulfonyl chloride → HCID 66973557, compound

HRID 1469114Notes

Reaction equation

HRID 1469114 reaction equation
[F:1][C:2]1[C:3]([N:9]=[CH:10][N:11]([CH3:13])[CH3:12])=[N:4][C:5]([OH:8])=[N:6][CH:7]=1.[C:14]1([S:20](Cl)(=[O:22])=[O:21])[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1>N1C=CC=CC=1>[C:14]1([S:20]([N:6]2[CH:7]=[C:2]([F:1])[C:3]([N:9]=[CH:10][N:11]([CH3:13])[CH3:12])=[N:4][C:5]2=[O:8])(=[O:22])=[O:21])[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1

Participants

4

Reactant 2

HCID 7369Benzenesulfonyl chlorideHCID 178484257HCID 178484257, compound

Product 1

HCID 66973557HCID 66973557, compoundYield 19%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

To an 8 mL screw-cap vial were added pyridine (2 mL), N′-(5-fluoro-2-hydroxy-pyrimidin-4-yl)-N,N-dimethylformamidine (100 mg, 0.54 mmol), and benzenesulfonyl chloride (106 mg, 0.60 mmol), and the mixture was shaken at room temperature for 24 hours (h). The crude mixture was partitioned between ethyl acetate (EtOAc) and saturated aqueous sodium bicarbonate (satd aq NaHCO3), and the organic phase was dried over magnesium sulfate (MgSO4), filtered, and evaporated to yield 153 mg of crude material. Reverse phase chromatography furnished the title product as a white solid (33 mg, 19%): mp 203-204° C.; 1H NMR (300 MHz, CDCl3) δ 8.77 (s, 1H), 8.16-8.11 (m, 3H), 7.72-7.65 (m, 1H) 7.60-7.53 (m, 2H), 3.24 (s, 3H), 3.23 (s, 3H); ESIMS m/z 325 ([M+H]+).

Workup

  1. customTo an 8 mL screw-cap vial
  2. customThe crude mixture was partitioned between ethyl acetate (EtOAc) and saturated aqueous sodium bicarbonate (satd aq NaHCO3)
  3. dry with materialthe organic phase was dried over magnesium sulfate (MgSO4)
  4. filtrationfiltered
  5. customevaporated
  6. customto yield 153 mg of crude material

Sources & evidence

ORD record
ord-5f4f0f78b79c49edb2761d23b0d0b746
Source dataset
uspto-grants-2015_04
Patent number
US09006259B2

Reaction notes

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