p-Toluenesulfonic acid monohydrate → HCID 20061283, compound

HRID 1085302Notes

Reaction equation

HRID 1085302 reaction equation
[CH3:1][CH:2]([NH:4][CH2:5][CH2:6][CH2:7][C:8]1[CH:13]=[CH:12][C:11]([N+:14]([O-:16])=[O:15])=[CH:10][CH:9]=1)[CH3:3].[CH3:17][N:18]1[C:23]([N:24]2CCCN(C3C=CC=CC=3[N+]([O-])=O)[CH2:26][CH2:25]2)=[CH:22][C:21](=[O:40])[N:20]([CH3:41])[C:19]1=[O:42].O.C1(C)C=CC(S(O)(=O)=O)=CC=1>C(#N)C>[CH3:17][N:18]1[C:23]([NH:24][CH2:25][CH2:26][N:4]([CH2:5][CH2:6][CH2:7][C:8]2[CH:9]=[CH:10][C:11]([N+:14]([O-:16])=[O:15])=[CH:12][CH:13]=2)[CH:2]([CH3:1])[CH3:3])=[CH:22][C:21](=[O:40])[N:20]([CH3:41])[C:19]1=[O:42]

Participants

5

Reactant 3

HCID 521998p-Toluenesulfonic acid monohydrateHCID 20061220HCID 20061220, compoundHCID 20061231HCID 20061231, compound2×

Product 1

HCID 20061283HCID 20061283, compoundYield 178.1%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

N-(1-methylethyl)-3-(4-nitrophenyl)propylamine (0.6 g), 0.5 g of 6-(1-aziridinyl)-1,3-dimethyl-2,4(1H,3H)-pyrimidinedione (compound 6) and 50 mg of p-toluenesulfonic acid monohydrate was dissolved in 30 ml acetonitrile, and then the solvent was removed in vacuo. The resultant oil was allowed to react at 80° C. for 3 hours and subjected to silica gel column chromatograph (chloroform/methanol=40:1 (v/v)) for purification. Thus, 1.0 g of 1,3-dimethyl-6-{2-[N-(1-methylethyl)-3-(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. customsubjected to silica gel column chromatograph (chloroform/methanol=40:1 (v/v)) for purification

Sources & evidence

ORD record
ord-772837cdfd2b4ea5891729fdccb8af16
Source dataset
uspto-grants-1991_04
Patent number
US05008267

Reaction notes

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