Dansyl chloride → HCID 18704796, compound

HRID 343375Notes

Reaction equation

HRID 343375 reaction equation
[CH3:1][N:2]([CH3:17])[C:3]1[CH:12]=[CH:11][CH:10]=[C:9]2[C:4]=1[CH:5]=[CH:6][CH:7]=[C:8]2[S:13](Cl)(=[O:15])=[O:14].[NH2:18][C:19]1[C:20]([O:27][CH3:28])=[N:21][C:22]([O:25][CH3:26])=[N:23][CH:24]=1>N1C=CC=CC=1>[CH3:1][N:2]([CH3:17])[C:3]1[CH:12]=[CH:11][CH:10]=[C:9]2[C:4]=1[CH:5]=[CH:6][CH:7]=[C:8]2[S:13]([NH:18][C:19]1[C:20]([O:27][CH3:28])=[N:21][C:22]([O:25][CH3:26])=[N:23][CH:24]=1)(=[O:15])=[O:14]

Participants

4

Reactant 2

HCID 11801Dansyl chlorideHCID 187048202,4-Dimethoxypyrimidin-5-amine

Product 1

HCID 18704796HCID 18704796, compoundYield 72.2%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Conditions

Temperature
0 °C

Procedure

5-Dimethylamino-1-naphthalenesulphonyl chloride (0.296 g) and 5-amino-2,4-dimethoxypyrimidine (0.155 g) were mixed together as solids. Pyridine (10 mls) was added and the solution was stirred at 0° C. for 30 minutes. The mixture was then heated at 80° C. for 5 hours. Volatile material was removed by evaporation and the residue was purified by elution with dichloromethane through a silica gel Mega Bond Elut column to give 5-dimethylamino-N-(2,4-dimethoxy-5-pyrimidinyl)-1-naphthalenesulphonamide (0.28 g), m.p. 201° C.; 1H NMR (d6 -DMSO): 2.85 (s, 6H), 3.1 (s, 3H), 3.8 (s, 3H), 7.3 (d, 1H), 7.55 (q, 2H); 7.95 (d, 1H), 8.05 (s, 1H), 8.30 (d, 1H), 8.48 (d, 1H), 9.85 (s, 1H); mass spectrum (+ve CI): 389 (M+H)+.

Workup

  1. temperatureThe mixture was then heated at 80° C. for 5 hours
  2. customVolatile material was removed by evaporation
  3. customthe residue was purified by elution with dichloromethane through a silica gel Mega Bond Elut column

Sources & evidence

ORD record
ord-4e10ffa7cd3f40c0820852a92d06d085
Source dataset
uspto-grants-1999_01
Patent number
US05861401

Reaction notes

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