Water → HCID 20061117, compound

HRID 1085288Notes

Reaction equation

HRID 1085288 reaction equation
[CH3:1][N:2]1[C:7]([NH:8][CH2:9][CH2:10][N:11]([CH2:15][CH2:16][CH2:17][C:18]2[CH:23]=[CH:22][C:21]([N+:24]([O-:26])=[O:25])=[CH:20][CH:19]=2)[CH2:12][CH2:13][OH:14])=[CH:6][C:5](=[O:27])[N:4]([CH3:28])[C:3]1=[O:29].[C:30](OC(=O)C)(=[O:32])[CH3:31].O>N1C=CC=CC=1>[CH3:1][N:2]1[C:7]([NH:8][CH2:9][CH2:10][N:11]([CH2:15][CH2:16][CH2:17][C:18]2[CH:19]=[CH:20][C:21]([N+:24]([O-:26])=[O:25])=[CH:22][CH:23]=2)[CH2:12][CH2:13][O:14][C:30](=[O:32])[CH3:31])=[CH:6][C:5](=[O:27])[N:4]([CH3:28])[C:3]1=[O:29]

Participants

5

Reactant 3

HCID 962WaterHCID 4486Nifekalant2×HCID 7918Acetic Anhydride

Product 1

HCID 20061117HCID 20061117, compoundYield 93.4%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

1.6 g of 1,3-dimethyl-6-{2-[N-(2-hydroxyethyl)-3-(4-nitrophenyl)propylamino]ethylamino}-2,4(1H,3H)-pyrimidinedione (Compound d) and 0.8 g of acetic anhydride were dissolved in 5 ml of pyridine. The resultant mixture was stirred at room temperature for 24 hours and then at 60° C. for 1 hour. The reaction mixture was poured into water and extracted with chloroform. The extract was washed with water and then concentrated. The residue was purified by chromatography on a silica gel column (eluent: chloroform/methanol=25/1-10/1, by volume), thereby obtaining 1.65 g of 1,3-dimethyl-6-{2-[N-(2-acetoxyethyl)-3-(4-nitrophenyl)propylamino]ethylamino}-2,4(1H,3H)-pyrimidinedione as crystals.

Workup

  1. extractionextracted with chloroform
  2. washThe extract was washed with water
  3. concentrationconcentrated
  4. customThe residue was purified by chromatography on a silica gel column (eluent: chloroform/methanol=25/1-10/1, by volume)

Sources & evidence

ORD record
ord-cdfe14a9b2ad47bc97cf3e08314b9275
Source dataset
uspto-grants-1991_04
Patent number
US05008267

Reaction notes

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