4-Nitrobenzaldehyde → 4-[2-(4-Nitrophenyl)ethenyl]pyrimidin-2-amine

HRID 2118952Notes

Reaction equation

HRID 2118952 reaction equation
[NH2:1][C:2]1[N:7]=[C:6]([CH3:8])[CH:5]=[CH:4][N:3]=1.[N+:9]([C:12]1[CH:19]=[CH:18][C:15]([CH:16]=O)=[CH:14][CH:13]=1)([O-:11])=[O:10].O.[OH-].[Na+]>C(O)=O>[N+:9]([C:12]1[CH:19]=[CH:18][C:15]([CH:16]=[CH:8][C:6]2[CH:5]=[CH:4][N:3]=[C:2]([NH2:1])[N:7]=2)=[CH:14][CH:13]=1)([O-:11])=[O:10]

Participants

6

Reactant 4

HCID 5414-NitrobenzaldehydeHCID 962WaterHCID 79392-Amino-4-methylpyrimidineHCID 14798Sodium Hydroxide

Product 1

HCID 537919064-[2-(4-Nitrophenyl)ethenyl]pyrimidin-2-amineYield 57.5%

Reagents, catalysts & solvents 1

HCID 284Formic AcidSolvent

Procedure

The starting compound is prepared as follows. A solution of 2-amino-4-methylpyrimidine (21.8 g) and p-nitrobenzaldehyde (30.2 g) in formic acid (45 ml) is refluxed (24 hours). After cooling, the reaction mixture is poured into water (1 liter), and the aqueous mixture is neutralized with a 5N sodium hydroxide solution. The crude product is extracted with chloroform, and the extract is dried over sodium sulfate and concentrated to dryness. The crude product is purified on a silica gel column to give 4-[2-(p-nitrophenyl)ethenyl]-2-aminopyrimidine (27.8 g), m.p. 214°-216° C., which is used for the next step without purification.

Workup

  1. customThe starting compound is prepared
  2. temperatureAfter cooling
  3. extractionThe crude product is extracted with chloroform
  4. dry with materialthe extract is dried over sodium sulfate
  5. concentrationconcentrated to dryness
  6. customThe crude product is purified on a silica gel column

Sources & evidence

ORD record
ord-7242a2cdd2554757a31e2330ff29fcd3
Source dataset
uspto-grants-1987_07
Patent number
US04681884

Reaction notes

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