Water → 2-Anilino-4-[1-isopropyl-2-(hydroxyiminomethyl)imidazol-5-yl]pyrimidine

HRID 32343

Reaction equation

HRID 32343 reaction equation
N1C=CC=CC=1.[NH:7]([C:14]1[N:19]=[C:18]([C:20]2[N:24]([CH:25]([CH3:27])[CH3:26])[C:23]([CH:28]=O)=[N:22][CH:21]=2)[CH:17]=[CH:16][N:15]=1)[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1.Cl.[NH2:31][OH:32].O>CCO>[NH:7]([C:14]1[N:19]=[C:18]([C:20]2[N:24]([CH:25]([CH3:27])[CH3:26])[C:23]([CH:28]=[N:31][OH:32])=[N:22][CH:21]=2)[CH:17]=[CH:16][N:15]=1)[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1

Participants

6

Reactant 4

HCID 962WaterHCID 1049PyridineHCID 443297Hydroxyamine hydrochlorideHCID 116381022-Anilino4-(2-formyl-1-isopropylimidazol-5-yl)pyrimidine

Product 1

HCID 1363744442-Anilino-4-[1-isopropyl-2-(hydroxyiminomethyl)imidazol-5-yl]pyrimidine

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Pyridine (283 μl, 3.50 mmol) was added to a solution of 2-anilino-4-(2-formyl-1-isopropylimidazol-5-yl)pyrimidine (Example 10; 250 mg, 0.814 mmol) and hydroxylamine.hydrochloride (283 mg, 4.07 mmol) in EtOH (8 ml) and the reaction mixture heated at reflux for 1 hr. The mixture was allowed to cool, water (10 ml) was added and the EtOH was removed by evaporation. Further water (10 ml) was added to the aqueous residue and the precipitated solid was collected by filtration, washed with water and dried to give the title compound as a 9:1 mixture of E and Z isomers (142 mg, 54%) as a white solid. NMR: Major isomer: 1.47 (d, 6H), 5.70 (m, 1H), 6.95 (t, 1H), 7.10 (d, 1H), 7.31 (t, 2H), 7.60 (s,1 H) 7.69 (d, 2H), 8.25 (s, 1H), 8.50 (d, 1H), 9.50 (s, 1H), 11.70 (s, 1 H); Minor isomer: 1.47 (d,6H), 5.70 (m, 1H), 6.95 (t, 1H), 7.19 (d, 1H), 7.31 (t, 2H), 7.69 (d, 2H), 7.78 (s, 1H), 8.10 (s, 1H), 8.52 (d, 1H), 9.57 (s, 1H), 13.89 (s, 1 H); m/z 323.

Workup

  1. temperaturethe reaction mixture heated
  2. temperatureat reflux for 1 hr
  3. temperatureto cool
  4. customthe EtOH was removed by evaporation
  5. additionFurther water (10 ml) was added to the aqueous residue
  6. filtrationthe precipitated solid was collected by filtration
  7. washwashed with water
  8. customdried

Sources & evidence

ORD record
ord-ea9d2c313a054777972219a5ea119fc5
Source dataset
uspto-grants-2008_09
Patent number
US07427626B2

Linked notes

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