Benzenesulfonyl chloride → HCID 59160627, compound

HRID 1500044Notes

Reaction equation

HRID 1500044 reaction equation
[F:1][C:2]1[C:3]([NH2:18])=[N:4][C:5]([O:8][CH2:9][C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=2[O:16][CH3:17])=[N:6][CH:7]=1.[Li+].C[Si]([N-][Si](C)(C)C)(C)C.[C:29]1([S:35](Cl)(=[O:37])=[O:36])[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1>C1COCC1>[F:1][C:2]1[C:3]([NH:18][S:35]([C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=2)(=[O:37])=[O:36])=[N:4][C:5]([O:8][CH2:9][C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=2[O:16][CH3:17])=[N:6][CH:7]=1

Participants

5

Reactant 3

HCID 7369Benzenesulfonyl chlorideHCID 2733832Lithium HexamethyldisilazideHCID 57819124HCID 57819124, compound

Product 1

HCID 59160627HCID 59160627, compoundYield 91.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a magnetically stirred solution of 5-fluoro-2-(2-methoxybenzyloxy)pyrimidin-4-amine (500 mg, 2.01 mmol) in dry THF (10 mL) was added 1M LiHMDS solution in THF (3.21 mL, 3.21 mmol) causing a slight exotherm. After stirring for 5 min, benzenesulfonyl chloride (0.346 mL, 2.71 mmol) was added and after 10 min the orange solution turned light orange and turbid. The mixture was stirred at room temperature for 5 h. The solvent was removed in vacuo and the resulting viscous gold oil was diluted in EtOAc (10 mL), poured into a separatory funnel containing EtOAc (100 mL) and washed with 1N HCl aqueous solution (4×50 mL) and brine solution (1×50 mL). The organic extract was dried over Na2SO4, filtered, and evaporated to yield N-(5-fluoro-2-(2-methoxybenzyloxy)pyrimidin-4-yl)benzenesulfonamide (714 mg, 91% yield) as a light tan solid. MS (ESI) m/z 387.99 (M−H)−.

Workup

  1. stirringThe mixture was stirred at room temperature for 5 h
  2. customThe solvent was removed in vacuo
  3. additionthe resulting viscous gold oil was diluted in EtOAc (10 mL)
  4. additionpoured into a separatory funnel
  5. additioncontaining EtOAc (100 mL)
  6. washwashed with 1N HCl aqueous solution (4×50 mL) and brine solution (1×50 mL)
  7. extractionThe organic extract
  8. dry with materialwas dried over Na2SO4
  9. filtrationfiltered
  10. customevaporated

Sources & evidence

ORD record
ord-0889484b189a46e2a9b1f0c8ad093806
Source dataset
uspto-grants-2015_12
Patent number
US09204653B2

Reaction notes

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