Pyridine → 2-Anilino-4-[1-isopropyl-2-(methoxyiminomethyl)imidazol-5-yl]pyrimidine

HRID 32344

Reaction equation

HRID 32344 reaction equation
Cl.[O:2]([NH2:4])[CH3:3].N1C=CC=CC=1.[NH:11]([C:18]1[N:23]=[C:22]([C:24]2[N:28]([CH:29]([CH3:31])[CH3:30])[C:27]([CH:32]=O)=[N:26][CH:25]=2)[CH:21]=[CH:20][N:19]=1)[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1>CCO>[NH:11]([C:18]1[N:23]=[C:22]([C:24]2[N:28]([CH:29]([CH3:30])[CH3:31])[C:27]([CH:32]=[N:4][O:2][CH3:3])=[N:26][CH:25]=2)[CH:21]=[CH:20][N:19]=1)[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1

Participants

5

Reactant 3

HCID 1049PyridineHCID 521874O-Methylhydroxylamine hydrochlorideHCID 116381022-Anilino4-(2-formyl-1-isopropylimidazol-5-yl)pyrimidine

Product 1

HCID 867607262-Anilino-4-[1-isopropyl-2-(methoxyiminomethyl)imidazol-5-yl]pyrimidineYield 91%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Methoxylamine hydrochloride (340 mg, 4.07 mmol) and pyridine (322 mg, 4.07 mmol) was added to a solution of 2-anilino-4-(2-formyl-1-isopropylimidazol-5-yl)pyrimidine (Example 10; 250 mg, 0.814 mmol) in EtOH (10 ml) and the mixture was stirred at ambient temperature for 18 hours. The volatiles were removed by evaporation and the residue triturated with water. The solid product was collected by filtration and dried at 50° C. under vacuum to give the title compound (248 mg, 91%) as a white crystalline solid. NMR (CDCl3): 1.54 (d, 6H), 4.07 (s, 3H), 5.65-5.80 (sept, 1H), 6.95 (d, 1H), 7.15 (m, 2H), 7.34 (t, 2H), 7.50 (s 1H), 7.57 (d, 2H), 8.28 (s, 1H), 8.41 (d, 1 H); m/z 337.

Workup

  1. customThe volatiles were removed by evaporation
  2. customthe residue triturated with water
  3. filtrationThe solid product was collected by filtration
  4. customdried at 50° C. under vacuum

Sources & evidence

ORD record
ord-1abed8ef4cef491fbb24b1d7b8cc1856
Source dataset
uspto-grants-2008_09
Patent number
US07427626B2

Linked notes

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