Water → HCID 20350283, compound

HRID 1449176Notes

Reaction equation

HRID 1449176 reaction equation
[CH:1]([OH:3])=O.C(OC(=O)C)(=O)C.[NH2:11][C:12]1[N:17]=[C:16]([NH2:18])[C:15]([CH2:19][C:20]2[CH:25]=[C:24]([O:26][CH3:27])[C:23]([O:28][CH3:29])=[C:22]([O:30][CH3:31])[CH:21]=2)=[CH:14][N:13]=1.O>N1C=CC=CC=1>[NH2:18][C:16]1[C:15]([CH2:19][C:20]2[CH:25]=[C:24]([O:26][CH3:27])[C:23]([O:28][CH3:29])=[C:22]([O:30][CH3:31])[CH:21]=2)=[CH:14][N:13]=[C:12]([NH:11][CH:1]=[O:3])[N:17]=1

Participants

5

Reactant 3

HCID 962WaterHCID 5578TrimethoprimHCID 19869020Acetic anhydride formic acid

Product 1

HCID 20350283HCID 20350283, compoundYield 75.5%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

2.64 g of formic acid/acetic acid anhydride are dripped, while cooling, into a suspension of 2.9 g of 2,4-diamino-5-(3,4,5-trimethoxybenzyl)-pyrimidine (trimethoprim) in 35 ml of pyridine and reacted at 50° to 60° C. for two hours. The reaction mixture is then poured into 400 ml of water and the precipitate is filtered off and recrystallized from a mixture of dimethylformamide and water. 2.4 g (75% of theory) of 4-amino-2-formamido-5-(3,4,5-trimethoxybenzyl)-pyrimidine of melting point 240° to 242° C. are obtained.

Workup

  1. customreacted at 50° to 60° C. for two hours
  2. filtrationthe precipitate is filtered off
  3. customrecrystallized from a mixture of dimethylformamide and water

Sources & evidence

ORD record
ord-37a7e21cc25149f294e60c3876e2d091
Source dataset
uspto-grants-1980_02
Patent number
US04189581

Reaction notes

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