Trimethoprim → 4-Amino-2-phenylacetamido-5-(3,4,5-trimethoxybenzyl)-pyrimidine

HRID 1449177Notes

Reaction equation

HRID 1449177 reaction equation
[NH2:1][C:2]1[N:7]=[C:6]([NH2:8])[C:5]([CH2:9][C:10]2[CH:15]=[C:14]([O:16][CH3:17])[C:13]([O:18][CH3:19])=[C:12]([O:20][CH3:21])[CH:11]=2)=[CH:4][N:3]=1.[C:22]1([CH2:28][C:29](Cl)=[O:30])[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1>ClC1C=CC=CC=1>[NH2:8][C:6]1[C:5]([CH2:9][C:10]2[CH:15]=[C:14]([O:16][CH3:17])[C:13]([O:18][CH3:19])=[C:12]([O:20][CH3:21])[CH:11]=2)=[CH:4][N:3]=[C:2]([NH:1][C:29](=[O:30])[CH2:28][C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)[N:7]=1

Participants

4

Reactant 2

HCID 5578TrimethoprimHCID 7679Phenylacetyl chloride

Product 1

HCID 203502984-Amino-2-phenylacetamido-5-(3,4,5-trimethoxybenzyl)-pyrimidine

Reagents, catalysts & solvents 1

HCID 7964ChlorobenzeneSolvent

Procedure

5.8 g of 2,4-diamino-5-(3,4,5-trimethoxybenzyl)-pyrimidine (trimethoprim) are suspended in 58 ml of chlorobenzene. At 125° C., 1.55 g of phenylacetyl chloride are dripped in, and the whole is maintained at this temperature for five hours. The difficultly soluble trimethoprim hydrochloride is filtered off and the filtrate is concentrated in vacuo. Upon recrystallization from ethanol there is obtained 4-amino-2-phenylacetamido-5-(3,4,5-trimethoxybenzyl)-pyrimidine of melting point 181° to 183° C.

Workup

  1. customAt 125° C.
  2. temperatureis maintained at this temperature for five hours
  3. filtrationThe difficultly soluble trimethoprim hydrochloride is filtered off
  4. concentrationthe filtrate is concentrated in vacuo
  5. customUpon recrystallization from ethanol

Sources & evidence

ORD record
ord-234f52a0e8fa4171a906792a71f101a4
Source dataset
uspto-grants-1980_02
Patent number
US04189581

Reaction notes

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