Water → HCID 67329050, compound

HRID 1846190Notes

Reaction equation

HRID 1846190 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][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][CH3:38])=[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>[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][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][CH3:38])=[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 hydrochlorideHCID 67356403HCID 67356403, compound

Product 1

HCID 67329050HCID 67329050, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To stirred solution containing 269 mg (0.52 mmol) of 5-(benzyloxy)-2-(2,5-dimethyl-1H-pyrrol-1-yl)-4-hexadecyl-6-methylpyrimidine in 10 mL of ethanol were added 723 mg (10.40 mmol) of hydroxylamine hydrochloride. The reaction mixture was then stirred at reflux during 5 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 231 mg (100%); silica gel TLC Rf 0.25 (1:1 hexanes-ethyl acetate); 1H NMR (CDCl3) δ 0.85 (t, 3H, J=6.8 Hz), 1.26 (m, 26H), 1.61 (quint, 2H, J=7.2 Hz), 2.28 (s, 3H), 2.56 (dd, 2H, J=7.6, 7.6 Hz), 4.72 (s, 2H), 5.03 (br s, 2H) and 7.35-7.40 (m, 5H); 13C NMR (CDCl3) δ 14.08, 18.91, 22.66, 28.42, 29.33, 29.41, 29.52, 29.63, 29.63, 29.63, 29.63, 29.67, 29.67, 29.67, 29.67, 29.73, 31.90, 75.88, 127, 88, 128.24, 128.24, 128.58, 128.58, 136.79, 142.87, 158.79, 161.12 and 164.87; mass spectrum (APCI), m/z 440.3646 (M+H)+ (C28H46N3O requires 440.3641).

Workup

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

Sources & evidence

ORD record
ord-dd433f1aaa5a4c5abbd6f5e31ee491e4
Source dataset
uspto-grants-2015_02
Patent number
US08952025B2

Reaction notes

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