Water → HCID 86710210, compound

HRID 2168213Notes

Reaction equation

HRID 2168213 reaction equation
[Cl:1][C:2]1[N:7]=[CH:6][NH:5][C:4]2=[N:8][CH:9]=[C:10]([Cl:11])[C:3]=12.[H-].[Na+].[C:14]1([S:20](Cl)(=[O:22])=[O:21])[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1.O>CN(C=O)C>[Cl:1][C:2]1[C:3]2[C:10]([Cl:11])=[CH:9][N:8]([S:20]([C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=3)(=[O:22])=[O:21])[C:4]=2[N:5]=[CH:6][N:7]=1

Participants

6

Reactant 4

HCID 962WaterHCID 7369Benzenesulfonyl chlorideHCID 24758Sodium hydrideHCID 178478276HCID 178478276, compound

Product 1

HCID 86710210HCID 86710210, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 4,5-dichloro-1H-pyrrolo[2,3-d]pyrimidine D39 (1 g) in DMF (20 ml) at 0° C. was added sodium hydride (60% w/w in mineral oil, 255 mg, 6.4 mmol) and the mixture stirred for 20 mins. Phenylsulfonyl chloride (1.31 g, 7.4 mmol) was the added dropwise and the reaction mixture was kept in a cool bath for 15 hours. The mixture was poured into water (40 ml), and the precipitate was filtered, washed with water and Et2O, dried in a vacuum to give the desired product D40 in 1.62 g as an ashen solid. LCMS [MH+] [email protected] min (5 min run)

Workup

  1. additionadded dropwise
  2. waitthe reaction mixture was kept in a cool bath for 15 hours
  3. filtrationthe precipitate was filtered
  4. washwashed with water and Et2O
  5. customdried in a vacuum

Sources & evidence

ORD record
ord-219fc69441014a82947bc6fb4f09e628
Source dataset
uspto-grants-2015_06
Patent number
US09045485B2

Reaction notes

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