p-Toluenesulfonic acid monohydrate → HCID 20061111, compound

HRID 1085300Notes

Reaction equation

HRID 1085300 reaction equation
[OH:1][CH2:2][CH2:3][CH2:4][NH:5][CH2:6][CH2:7][CH2:8][C:9]1[CH:14]=[CH:13][C:12]([N+:15]([O-:17])=[O:16])=[CH:11][CH:10]=1.[CH3:18][N:19]1[C:24]([N:25]2CCCN(C3C=CC=CC=3[N+]([O-])=O)[CH2:27][CH2:26]2)=[CH:23][C:22](=[O:41])[N:21]([CH3:42])[C:20]1=[O:43].O.C1(C)C=CC(S(O)(=O)=O)=CC=1>C(#N)C>[CH3:18][N:19]1[C:24]([NH:25][CH2:26][CH2:27][N:5]([CH2:6][CH2:7][CH2:8][C:9]2[CH:10]=[CH:11][C:12]([N+:15]([O-:17])=[O:16])=[CH:13][CH:14]=2)[CH2:4][CH2:3][CH2:2][OH:1])=[CH:23][C:22](=[O:41])[N:21]([CH3:42])[C:20]1=[O:43]

Participants

5

Reactant 3

HCID 521998p-Toluenesulfonic acid monohydrateHCID 20061231HCID 20061231, compound2×HCID 20061328HCID 20061328, compound

Product 1

HCID 20061111HCID 20061111, compoundYield 109.9%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

N-(3-hydroxypropyl)-3-(4-nitrophenyl)propylamine (0.7 g), 0.53 g of 6-(1-aziridinyl)-1,3-dimethyl-2,4(1H,3H)-pyrimidinedione (compound 6) and 50 mg of p-toluene-sulfonic acid monohydrate were dissolved in 30 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 subjected to silica gel column chromatograph (chloroform/methanol=40:1 (v/v)) for purification: 0.68 g of 1,3-dimethyl-6-{2-[N-(3-hydroxypropyl)-3-(4-nitrophenyl)propylamino]ethylamino}-2,4(1H,3H)-pyrimidinedione was thus 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-eeaf06b0962642949f5ec0bcbde6f1f2
Source dataset
uspto-grants-1991_04
Patent number
US05008267

Reaction notes

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