Trimethoprim → HCID 20350284, compound

HRID 1449178Notes

Reaction equation

HRID 1449178 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(N(CC)CC)C.[CH2:29]([O:31][CH2:32][C:33](Cl)=[O:34])[CH3:30]>C(Cl)(Cl)Cl>[CH2:29]([O:31][CH2:32][C:33]([NH:21][C:17]1[N:18]=[C:19]([NH2:20])[C:14]([CH2:13][C:5]2[CH:6]=[C:7]([O:11][CH3:12])[C:8]([O:9][CH3:10])=[C:3]([O:2][CH3:1])[CH:4]=2)=[CH:15][N:16]=1)=[O:34])[CH3:30]

Participants

5

Reactant 3

HCID 5578TrimethoprimHCID 8471TriethylamineHCID 84189Ethoxyacetyl chloride

Product 1

HCID 20350284HCID 20350284, compound

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Conditions

Temperature
50 °C

Procedure

5.8 g of trimethoprim are suspended in 80 ml of chloroform. After addition of 4 g of triethylamine 2.5 g of ethoxyacetyl chloride are dripped in at room temperature. The mixture is stirred for another hour at 50° C. and then cooled. The triethylammonium chloride is separated by filtration, the filtrate is concentrated and the residue is recrystallized from isopropanol. 4 g of 2-ethoxyacetamido-4-amino-5-(3,4,5-trimethoxybenzyl)-pyrimidine of melting point 175° to 176° C. are obtained.

Workup

  1. customare dripped in at room temperature
  2. temperaturecooled
  3. customThe triethylammonium chloride is separated by filtration
  4. concentrationthe filtrate is concentrated
  5. customthe residue is recrystallized from isopropanol

Sources & evidence

ORD record
ord-ea874e8756d2492d9d107e3d759be17c
Source dataset
uspto-grants-1980_02
Patent number
US04189581

Reaction notes

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