p-Toluenesulfonic acid monohydrate → HCID 20061408, compound

HRID 1085306Notes

Reaction equation

HRID 1085306 reaction equation
[CH3:1][N:2]1[C:7]([N:8]2CCCN(C3C=CC=CC=3[N+]([O-])=O)[CH2:10][CH2:9]2)=[CH:6][C:5](=[O:24])[N:4]([CH3:25])[C:3]1=[O:26].[OH:27][CH2:28][CH2:29][NH:30][CH2:31][CH2:32][CH2:33][C:34]1[CH:39]=[CH:38][C:37]([N+:40]([O-:42])=[O:41])=[C:36]([O:43][CH3:44])[CH:35]=1.[OH2:45].C1(C)C=CC(S(O)(=O)=O)=CC=1.C(Cl)(Cl)Cl.[CH3:61][OH:62]>C(#N)C>[C:3]([OH:26])(=[O:27])[C:61]([OH:62])=[O:45].[CH3:1][N:2]1[C:7]([NH:8][CH2:9][CH2:10][N:30]([CH2:31][CH2:32][CH2:33][C:34]2[CH:39]=[CH:38][C:37]([N+:40]([O-:42])=[O:41])=[C:36]([O:43][CH3:44])[CH:35]=2)[CH2:29][CH2:28][OH:27])=[CH:6][C:5](=[O:24])[N:4]([CH3:25])[C:3]1=[O:26]

Participants

6

Reactant 4

HCID 521998p-Toluenesulfonic acid monohydrateHCID 20061231HCID 20061231, compound2×HCID 20061422HCID 20061422, compoundHCID 21584188Chloroform methanol

Product 1

HCID 20061408HCID 20061408, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

6-(1-aziridinyl)-1,3-dimethyl-2,4(1H,3H)-pyrimidinedione (compound 6) (0.45 g), 0.7 g of N-(2-hydroxyethyl)-3-(3-methoxy-4-nitrophenyl)propylamine and 50 mg of p-toluenesulfonic acid monohydrate was dissolved in 25 ml of acetonitrile and then the solvent was removed in vacuo. The resultant oil was allowed to react at 80° C. for 3 hours and then subjected to silica gel column chromatograph (chloroform/methanol=40/1, v/v) for purification; thereby 0.38 g of an oil, 1,3-dimethyl-6-{2-[N-(2-hydroxethyl)-3-(3-methoxy-4-nitrophenyl)propylamino]ethylamino}-2,4(1H,3H)-pyrimidinedione, was obtained.

Workup

  1. customthe solvent was removed in vacuo
  2. customto react at 80° C. for 3 hours
  3. customv/v) for purification

Sources & evidence

ORD record
ord-69284ebb6ddd49cd903a43a5546ad6f0
Source dataset
uspto-grants-1991_04
Patent number
US05008267

Reaction notes

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