Water → N-(4-Amino-5-(3,4,5-trimethoxybenzyl)-2-pyrimidinyl)phthalimide

HRID 1449179Notes

Reaction equation

HRID 1449179 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH2:13][C:14]2[CH:15]=[N:16][C:17]([NH2:21])=[N:18][C:19]=2[NH2:20])[CH:6]=[C:7]([O:11][CH3:12])[C:8]=1[O:9][CH3:10].[C:22]1(=O)[O:27][C:25](=[O:26])[C:24]2=[CH:28][CH:29]=[CH:30][CH:31]=[C:23]12.O>N1C=CC=CC=1>[C:22]1(=[O:27])[N:21]([C:17]2[N:18]=[C:19]([NH2:20])[C:14]([CH2:13][C:5]3[CH:6]=[C:7]([O:11][CH3:12])[C:8]([O:9][CH3:10])=[C:3]([O:2][CH3:1])[CH:4]=3)=[CH:15][N:16]=2)[C:25](=[O:26])[C:24]2=[CH:28][CH:29]=[CH:30][CH:31]=[C:23]12

Participants

5

Reactant 3

HCID 962WaterHCID 5578TrimethoprimHCID 6811Phthalic Anhydride

Product 1

HCID 163307N-(4-Amino-5-(3,4,5-trimethoxybenzyl)-2-pyrimidinyl)phthalimideYield 55.6%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

8.7 g of trimethoprim are dissolved in 50 ml of pyridine at about 50° C., and then 4.5 g of phthalic anhydride are added. The mixture is stirred for another two hours at from 80° to 90° C.; after cooling, 100 ml of water are added. The precipitate is washed with water and recrystallized from ethanol. 7 g of 2-phthalimido-4-amino-5-(3,4,5-trimethoxybenzyl)-pyrimidine of melting point 221° C. are obtained as intermediate product.

Workup

  1. temperatureafter cooling
  2. washThe precipitate is washed with water
  3. customrecrystallized from ethanol

Sources & evidence

ORD record
ord-f0512285698f4c21b8a624eb62b7c872
Source dataset
uspto-grants-1980_02
Patent number
US04189581

Reaction notes

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