Water → HCID 54064100, compound

HRID 251500Notes

Reaction equation

HRID 251500 reaction equation
[O:1]([C:8]1[CH:13]=[CH:12][C:11]([C:14]2[C:22]3[C:21]([NH2:23])=[N:20][CH:19]=[N:18][C:17]=3[NH:16][CH:15]=2)=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[H-].[Na+].[CH:26]([S:29](Cl)(=[O:31])=[O:30])([CH3:28])[CH3:27].O>CN(C)C=O>[CH:26]([S:29]([N:16]1[C:17]2[N:18]=[CH:19][N:20]=[C:21]([NH2:23])[C:22]=2[C:14]([C:11]2[CH:10]=[CH:9][C:8]([O:1][C:2]3[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=3)=[CH:13][CH:12]=2)=[CH:15]1)(=[O:31])=[O:30])([CH3:28])[CH3:27]

Participants

6

Reactant 4

HCID 962WaterHCID 24758Sodium hydrideHCID 824082-Propanesulfonyl chlorideHCID 120422345-(4-phenoxyphenyl)-7H-pyrrolo[2,3-d]pyrimidin-4-ylamine

Product 1

HCID 54064100HCID 54064100, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

5-(4-Phenoxyphenyl)-7H-pyrrolo[2,3-d]pyrimidin-4-ylamine (1.57 g) was dissolved in dry dimethylformamide (30 ml) and then sodium hydride (0.22 g of a 60% dispersion in mineral oil) was added with stirring. The mixture was stirred for 30 minutes and then isopropylsulphonyl chloride (0.74 g) was added and the mixture was stirred at ambient temperature for 18 hours. Water was added to the mixture until no further precipitation occurred. The solid was collected by filtration and purified by flash column chromatography on silica using dichloromethane/methanol (9:1) as the mobile phase to give a solid which was further purified by flash column chromatography on silica using ethyl acetate as the mobile phase to give 7-isopropylsulphonyl-5-(4-phenoxyphenyl)-7H-pyrrolo[2,3-d]pyrimidin-4-ylamine, m.p. 162-162.5° C.

Workup

  1. stirringThe mixture was stirred for 30 minutes
  2. stirringthe mixture was stirred at ambient temperature for 18 hours
  3. filtrationThe solid was collected by filtration
  4. custompurified by flash column chromatography on silica
  5. customto give a solid which
  6. customwas further purified by flash column chromatography on silica

Sources & evidence

ORD record
ord-619253608462445ab8a90bddc09fc23d
Source dataset
uspto-grants-2011_01
Patent number
US07863444B2

Reaction notes

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