Sodium hydride → Propane-1-sulfonic acid [2-amino-6-(2,6-dichlorophenyl)-pyrido[2,3-d]pyrimidin-7-yl]-amide

HRID 3477

Reaction equation

HRID 3477 reaction equation
[NH2:1][C:2]1[N:3]=[CH:4][C:5]2[CH:11]=[C:10]([C:12]3[C:17]([Cl:18])=[CH:16][CH:15]=[CH:14][C:13]=3[Cl:19])[C:9]([NH2:20])=[N:8][C:6]=2[N:7]=1.[H-].[Na+].[CH2:23]([S:26](Cl)(=[O:28])=[O:27])[CH2:24][CH3:25]>CN(C=O)C>[NH2:1][C:2]1[N:3]=[CH:4][C:5]2[CH:11]=[C:10]([C:12]3[C:17]([Cl:18])=[CH:16][CH:15]=[CH:14][C:13]=3[Cl:19])[C:9]([NH:20][S:26]([CH2:23][CH2:24][CH3:25])(=[O:28])=[O:27])=[N:8][C:6]=2[N:7]=1

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 662791-Propanesulfonyl chlorideHCID 53281136-(2,6-Dichlorophenyl)pyrido[2,3-d]pyrimidine-2,7-diamine

Product 1

HCID 53755885Propane-1-sulfonic acid [2-amino-6-(2,6-dichlorophenyl)-pyrido[2,3-d]pyrimidin-7-yl]-amide

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a slurry of 1.00 g of 2,7-diamino-6-(2,6-dichlorophenyl)-pyrido[2,3-d]pyrimidine from Example 1 in 15 mL of DMF was added 0.15 g sodium hydride (60% in mineral oil) portionwise and the mixture stirred for 1 hour. Propanesulfonyl chloride (0.39 mL) is added dropwise, and the reaction mixture stirred at ambient temperature for 16 hours. The reaction mixture is filtered to remove a small amount of insoluble material and the filtrate evaporated in vacuo. The product is purified by medium pressure liquid chromatography (MPLC) using silica gel and eluting with a gradient of CHCl3 :EtOAc (2:1) to CHCl3 :EtOAc (1:1) to afford the title compound.

Workup

  1. stirringthe reaction mixture stirred at ambient temperature for 16 hours
  2. filtrationThe reaction mixture is filtered
  3. customto remove a small amount of insoluble material
  4. customthe filtrate evaporated in vacuo
  5. customThe product is purified by medium pressure liquid chromatography (MPLC)
  6. washeluting with a gradient of CHCl3 :EtOAc (2:1) to CHCl3 :EtOAc (1:1)

Sources & evidence

ORD record
ord-587171f404ec4562b7f202a047a9a693
Source dataset
uspto-grants-1998_03
Patent number
US05733913

Linked notes

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