Hydroxyamine hydrochloride → HCID 67328311, compound

HRID 1846145Notes

Reaction equation

HRID 1846145 reaction equation
CC1[N:3]([C:8]2[N:13]=[C:12]([CH3:14])[C:11]([O:15][CH2:16][C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=3)=[C:10]([CH3:23])[N:9]=2)C(C)=CC=1.Cl.NO>C(O)C.O.O>[NH2:3][C:8]1[N:13]=[C:12]([CH3:14])[C:11]([O:15][CH2:16][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)=[C:10]([CH3:23])[N:9]=1

Participants

5

Reactant 2

HCID 443297Hydroxyamine hydrochlorideHCID 67353995HCID 67353995, compound

Product 1

HCID 67328311HCID 67328311, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 19096565Water ethanolSolvent

Procedure

To a stirred solution containing 2.85 g (9.27 mmol) 2-(2,5-dimethyl-1H-pyrrol-1-yl)-5-benzyloxy-4,6-dimethylpyrimidine (6) in 30 mL of ethanol-water 1:1 were added 6.44 g (93 mmol) of hydroxylamine hydrochloride. The reaction mixture was stirred at reflux overnight under argon atmosphere. The pH of the solution was then brought to 10 and diluted with 20 mL of water. The mixture was extracted with two portions of 30 mL of dichloromethane. The combined organic solution was dried (MgSO4) and then concentrate under diminished pressure. The residue was purified by chromatography on a silica gel column. Elution with acetone-hexanes 1:2 gave the expected product as white solid. Yield: 2.1 g (98%). 1H-NMR (CDCl3) δ 7.39 (m, 5H), 4.80 (br. 2H), 4.74 (s, 2H), 2.29 (s, 6H). 13C-NMR (CDCl3) 160.05, 158.45, 141.50, 137.02, 37.27, 19.22.

Workup

  1. temperatureat reflux overnight under argon atmosphere
  2. extractionThe mixture was extracted with two portions of 30 mL of dichloromethane
  3. dry with materialThe combined organic solution was dried (MgSO4)
  4. concentrationconcentrate under diminished pressure
  5. customThe residue was purified by chromatography on a silica gel column
  6. washElution with acetone-hexanes 1:2

Sources & evidence

ORD record
ord-1088901b215c42c5ba60b05a09161f9a
Source dataset
uspto-grants-2015_02
Patent number
US08952025B2

Reaction notes

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