Dansyl chloride → 5-dimethylamino-N-(2-chloro-4-methoxy-5-pyrimidinyl)-1-naphthalenesulphonamide

HRID 343377Notes

Reaction equation

HRID 343377 reaction equation
[H-].[Na+].[NH2:3][C:4]1[C:5]([O:11][CH3:12])=[N:6][C:7]([Cl:10])=[N:8][CH:9]=1.[H][H].[CH3:15][N:16]([CH3:31])[C:17]1[CH:26]=[CH:25][CH:24]=[C:23]2[C:18]=1[CH:19]=[CH:20][CH:21]=[C:22]2[S:27](Cl)(=[O:29])=[O:28]>COCCOC>[CH3:15][N:16]([CH3:31])[C:17]1[CH:26]=[CH:25][CH:24]=[C:23]2[C:18]=1[CH:19]=[CH:20][CH:21]=[C:22]2[S:27]([NH:3][C:4]1[C:5]([O:11][CH3:12])=[N:6][C:7]([Cl:10])=[N:8][CH:9]=1)(=[O:29])=[O:28]

Participants

6

Reactant 4

HCID 11801Dansyl chlorideHCID 24758Sodium hydrideHCID 211863562-Chloro-4-methoxypyrimidin-5-amineHCID 178418361HCID 178418361, compound

Product 1

HCID 187048045-dimethylamino-N-(2-chloro-4-methoxy-5-pyrimidinyl)-1-naphthalenesulphonamideYield 17.1%

Reagents, catalysts & solvents 1

HCID 80711,2-DimethoxyethaneSolvent

Procedure

Sodium hydride (60% dispersion in oil; 0.1 g) was added to a solution of 5-amino-2-chloro-4-methoxypyrimidine (0.159 g) in 1,2-dimethoxyethane (10 ml). When evolution of hydrogen had ceased, 5-dimethylamino-1-naphthalenesulphonyl chloride (0.336 g) was added and the solution was stirred for 2 hours. Volatile material was then removed by evaporation. The residue was purified by elution with ethyl acetate/hexane/acetic acid (0-20% ethyl acetate, 0.1% acetic acid) through a silica gel Mega Bond Elut column to give 5-dimethylamino-N-(2-chloro-4-methoxy-5-pyrimidinyl)-1-naphthalenesulphonamide (0.067 g) as an oil; 1H NMR (d6 -DMSO): 2.85 (s, 6H), 3.39 (s, 3H), 7.3 (d, 1H), 7.6 (t of t, 2H), 8.08 (d, 1H), 8.25 (s, 1H), 8.30 (d, 1H), 8.5 (d, 1H), 10.42 (s, 1H); mass spectrum (+ve FAB, dichloromethane/NBA): 393 (M+H)+.

Workup

  1. customVolatile material was then removed by evaporation
  2. customThe residue was purified by elution with ethyl acetate/hexane/acetic acid (0-20% ethyl acetate, 0.1% acetic acid) through a silica gel Mega Bond Elut column

Sources & evidence

ORD record
ord-e9c46147961c4479b3e44ba1c60dd707
Source dataset
uspto-grants-1999_01
Patent number
US05861401

Reaction notes

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