Dimethylsulphamoyl chloride → 6-(2,4-Diamino-pyrimidin-5-ylmethyl)-4-ethoxy-indole-1-sulfonic Acid Dimethylamide

HRID 48456Notes

Reaction equation

HRID 48456 reaction equation
CC([O-])(C)C.[K+].[CH2:7]([O:9][C:10]1[CH:18]=[C:17]([CH2:19][C:20]2[C:21]([NH2:27])=[N:22][C:23]([NH2:26])=[N:24][CH:25]=2)[CH:16]=[C:15]2[C:11]=1[CH:12]=[CH:13][NH:14]2)[CH3:8].[CH3:28][N:29]([CH3:34])[S:30](Cl)(=[O:32])=[O:31]>CN(C)C=O>[CH3:28][N:29]([CH3:34])[S:30]([N:14]1[C:15]2[C:11](=[C:10]([O:9][CH2:7][CH3:8])[CH:18]=[C:17]([CH2:19][C:20]3[C:21]([NH2:27])=[N:22][C:23]([NH2:26])=[N:24][CH:25]=3)[CH:16]=2)[CH:12]=[CH:13]1)(=[O:32])=[O:31]

Participants

5

Reactant 3

HCID 83372Dimethylsulphamoyl chlorideHCID 227429195-(4-Ethoxy-1H-indol-6-ylmethyl)-pyrimidine-2,4-diamineHCID 23665647Potassium tert-butoxide

Product 1

HCID 699205526-(2,4-Diamino-pyrimidin-5-ylmethyl)-4-ethoxy-indole-1-sulfonic Acid DimethylamideYield 53%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Potassium tert-butylate (42 mg, 0.37 mmol) was added to a solution of 5-(4-ethoxy-1H-indol-6-ylmethyl)-pyrimidine-2,4-diamine (Example 1; 100 mg, 0.353 mmol) in N,N-dimethylformamide (5 mL). After 15 min dimethylsulfamoyl chloride (53 mg, 0.37 mmol) was added, then after 30 min the solvent was distilled off and the residue partitioned between ethyl acetate and saturated aqueous sodium hydrogencarbonate solution. The organic layer was washed with brine, dried (MgSO4), and evaporated. Suspension of the residue in ether and collection of the precipitate afforded the title compound (73 mg, 53%). Off-white solid.

Workup

  1. distillationafter 30 min the solvent was distilled off
  2. customthe residue partitioned between ethyl acetate and saturated aqueous sodium hydrogencarbonate solution
  3. washThe organic layer was washed with brine
  4. dry with materialdried (MgSO4)
  5. customevaporated
  6. additionSuspension of the residue in ether
  7. customcollection of the precipitate

Sources & evidence

ORD record
ord-8658b4d0de8f49fdbec462b7b9b6e592
Source dataset
uspto-grants-2004_03
Patent number
US06703397B2

Reaction notes

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