Water → HCID 67328339, compound

HRID 1846186Notes

Reaction equation

HRID 1846186 reaction equation
[CH2:1]([O:8][C:9]1[C:10]([CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH3:32])=[N:11][C:12]([N:16]2C(C)=CC=C2C)=[N:13][C:14]=1[CH3:15])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Cl.NO.O.[OH-].[Na+]>C(O)C.O>[CH2:1]([O:8][C:9]1[C:10]([CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH3:32])=[N:11][C:12]([NH2:16])=[N:13][C:14]=1[CH3:15])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 4

HCID 962WaterHCID 14798Sodium HydroxideHCID 443297Hydroxyamine hydrochloride2×HCID 67356396HCID 67356396, compound

Product 1

HCID 67328339HCID 67328339, compound

Reagents, catalysts & solvents 1

HCID 19096565Water ethanolSolvent

Procedure

To stirred solution containing 502 mg (1.15 mmol) of 5-(benzyloxy)-4-decyl-2-(2,5-dimethyl-1H-pyrrol-1-yl)-6-methylpyrimidine in 10 mL of ethanol-water 9:1 were added 800 mg (11.50 mmol) of hydroxylamine hydrochloride. The reaction mixture was then stirred at reflux during 5 h. A second portion of 800 mg (11.50 mmol) of hydroxylamine hydrochloride was added and the reaction mixture was stirred at reflux for 16 h. The reaction mixture was then poured into 70 mL of water and then basified to a pH 9-10 with a 1N NaOH aqueous solution. The mixture was extracted with two 70-mL portions of ethyl acetate. The combined organic layer was washed with a 70-mL portion of brine, dried (MgSO4) and then concentrated under diminished pressure. The residue was purified by chromatography on a silica gel column (10×3 cm). Elution with 3:2 hexanes-ethyl acetate afforded the expected product as a colorless oil: yield 305 mg (75%); silica gel TLC Rf 0.25 (3:2 hexanes-ethyl acetate); 1H NMR (CDCl3) δ 0.85 (t, 3H, J=6.4 Hz), 1.26 (m, 14H), 1.61 (m, 2H), 2.27 (s, 3H), 2.56 (dd, 2H, J=8.0, 8.0 Hz), 4.71 (s, 2H), 5.24 (br s, 2H) and 7.35-7.40 (m, 5H); 13C NMR (CDCl3) δ 13.94, 18.86, 22.64, 28.41, 29.27, 29.39, 29.50, 29.55, 29.71, 31.87, 31.88, 75.88, 127, 88, 128.24, 128.24, 128.58, 128.58, 136.79, 142.8, 158.92, 161.09 and 162.82; mass spectrum (APCI), m/z 356.2704 (M+H)+ (C22H34N3O requires 356.2702).

Workup

  1. stirringThe reaction mixture was then stirred
  2. temperatureat reflux during 5 h
  3. stirringthe reaction mixture was stirred
  4. temperatureat reflux for 16 h
  5. extractionThe mixture was extracted with two 70-mL portions of ethyl acetate
  6. washThe combined organic layer was washed with a 70-mL portion of brine
  7. dry with materialdried (MgSO4)
  8. concentrationconcentrated under diminished pressure
  9. customThe residue was purified by chromatography on a silica gel column (10×3 cm)
  10. washElution with 3:2 hexanes-ethyl acetate

Sources & evidence

ORD record
ord-142918920d2e4a88ad2f8dae4f285a2a
Source dataset
uspto-grants-2015_02
Patent number
US08952025B2

Reaction notes

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