Diazomethane → HCID 17774515, compound

HRID 378280Notes

Reaction equation

HRID 378280 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([NH:11][C:12]2[CH:17]=[C:16]([NH:18][CH3:19])[N:15]=[C:14]([NH:20][CH3:21])[N:13]=2)(=[O:10])=[O:9])=[CH:4][CH:3]=1.[N+](=[CH2:24])=[N-]>CO.CN(C)C=O.C(OCC)C>[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([N:11]([C:12]2[CH:17]=[C:16]([NH:18][CH3:19])[N:15]=[C:14]([NH:20][CH3:21])[N:13]=2)[CH3:24])(=[O:10])=[O:9])=[CH:4][CH:3]=1

Participants

6

Reactant 2

HCID 9550DiazomethaneHCID 53121454-Amino-N-[2,6-bis(methylamino)pyrimidin-4-yl]benzenesulfonamide

Product 1

HCID 17774515HCID 17774515, compoundYield 35%

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 3283Diethyl EtherSolventHCID 6228DimethylformamideSolvent

Procedure

0.65 g (0.0021 mol) of 4-amino-N-(2,6-bis-methylamino-pyrimidin-4-yl)-benzenesulfonamide was dissolved in a mixture of 100 ml of methanol and 400 ml of dimethylformamide and treated with 60 ml of a solution of diazomethane in diethyl ether. The mixture was stirred at room temperature for 30 minutes. The solvent was distilled off and the residue was chromatographed over 50 g of SiO2 with 5% of methanol in methylene chloride as the eluent. There was obtained 0.24 g (35%) of 4-amino-N-(2,6-bis-methylamino-pyrimidin-4-yl)-N-methyl-benzenesulfonamide as a yellow solid; m.p.: 79-80° C.

Workup

  1. distillationThe solvent was distilled off
  2. customthe residue was chromatographed over 50 g of SiO2 with 5% of methanol in methylene chloride as the eluent

Sources & evidence

ORD record
ord-23b240bec1724a26857f8df5f1ae4309
Source dataset
uspto-grants-2000_02
Patent number
US06030976

Reaction notes

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