Sodium hydride → 7-cyclopentanesulphonyl-5-(4-phenoxyphenyl)-7H-pyrrolo[2,3-d]pyrimidin-4-ylamine

HRID 51504

Reaction equation

HRID 51504 reaction equation
[H-].[Na+].[O:3]([C:10]1[CH:15]=[CH:14][C:13]([C:16]2[C:24]3[C:23]([NH2:25])=[N:22][CH:21]=[N:20][C:19]=3[NH:18][CH:17]=2)=[CH:12][CH:11]=1)[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.[CH:26]1([S:31](Cl)(=[O:33])=[O:32])[CH2:30][CH2:29][CH2:28][CH2:27]1>CN(C)C=O>[CH:26]1([S:31]([N:18]2[C:19]3[N:20]=[CH:21][N:22]=[C:23]([NH2:25])[C:24]=3[C:16]([C:13]3[CH:12]=[CH:11][C:10]([O:3][C:4]4[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=4)=[CH:15][CH:14]=3)=[CH:17]2)(=[O:33])=[O:32])[CH2:30][CH2:29][CH2:28][CH2:27]1

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 3717197Cyclopentanesulfonyl chlorideHCID 120422345-(4-phenoxyphenyl)-7H-pyrrolo[2,3-d]pyrimidin-4-ylamine

Product 1

HCID 227362647-cyclopentanesulphonyl-5-(4-phenoxyphenyl)-7H-pyrrolo[2,3-d]pyrimidin-4-ylamine

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

Sodium hydride (0.132 g of a 60% dispersion in mineral oil) was added to a solution of 5-(4-phenoxyphenyl)-7H-pyrrolo[2,3-d]pyrimidin-4-ylamine (1.0 g) in dry dimethylformamide (30 ml) with stirring under nitrogen. The mixture was stirred for 30 minutes and then cyclopentanesulphonyl chloride (0.558 g, prepared as described in J.O.C.1952, 17, 1529-1533) in dry dimethylformamide (5 ml) was added dropwise. The mixture was allowed to stand for 72 hours and then evaporated under vacuum. The residue was triturated with water and filtered to give a solid which was washed well with water, then stirred with ethyl acetate then filtered. The filtrate was purified by flash column chromatography on silica using ethyl acetate as the mobile phase. Appropriate fractions were collected and evaporated to give 7-cyclopentanesulphonyl-5-(4-phenoxyphenyl)-7H-pyrrolo[2,3-d]pyrimidin-4-ylamine, m.p. 188-188.5° C.

Workup

  1. stirringThe mixture was stirred for 30 minutes
  2. customevaporated under vacuum
  3. customThe residue was triturated with water
  4. filtrationfiltered
  5. customto give a solid which
  6. washwas washed well with water
  7. stirringstirred with ethyl acetate
  8. filtrationthen filtered
  9. customThe filtrate was purified by flash column chromatography on silica
  10. customAppropriate fractions were collected
  11. customevaporated

Sources & evidence

ORD record
ord-0f39989a47c3411ba5b41a7b11f29bcc
Source dataset
uspto-grants-2004_03
Patent number
US06713474B2

Linked notes

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