Potassium Hydroxide → HCID 67327945, compound

HRID 1846144Notes

Reaction equation

HRID 1846144 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]([CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][O:33][CH2:34][C:35]3[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=3)[N:9]=2)C(C)=CC=1.Cl.NO.[OH-].[K+].[OH-].[Na+]>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]([CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][O:33][CH2:34][C:35]2[CH:36]=[CH:37][CH:38]=[CH:39][CH:40]=2)[N:9]=1

Participants

7

Reactant 4

HCID 14797Potassium HydroxideHCID 14798Sodium HydroxideHCID 443297Hydroxyamine hydrochloride2×HCID 67355138HCID 67355138, compound

Product 1

HCID 67327945HCID 67327945, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 19096565Water ethanolSolvent

Procedure

To stirred solution containing 343 mg (0.63 mmol) of 2-(2,5-dimethyl-1H-pyrrol-1-yl)-5-benzyloxy-4-methyl-6-(10-benzyloxydecyl)-pyrimidine (7) in 10 mL of ethanol-water 9:1 were added 500 mg (7.19 mmol) of hydroxylamine hydrochloride followed by 400 mg (7.14 mmol) of potassium hydroxide. The reaction mixture was then stirred at reflux under argon atmosphere overnight. A second portion of 500 mg (7.19 mmol) of hydroxylamine hydrochloride was added and the reaction mixture was stirred overnight at reflux under argon atmosphere. The reaction mixture was then poured into 70 mL of water and then basified to a pH 9-10 with a 1N NaOH solution. The mixture was extracted with two portions of 70 mL of dichloromethane. The combined organic solution was washed with a portion of 70 mL of brine, dried (MgSO4) and then concentrated under diminished pressure. The residue was purified by chromatography on a silica gel column. Elution with acetone-hexanes 2:1 gave the expected product as a colorless oil: yield 153 mg (52%). 1H-NMR (CDCl3) δ 7.48-7.37 (m, 10H), 5.17 (br., 2H), 4.69 (s, 2H), 4.45 (s, 2H), 3.41 (t, 2H, J=6.8), 2.55 (t, 2H, J=7.6), 2.26 (s, 3H), 1.63-1.53 (m, 4H), 1.27 (m, 12H); 13C-NMR (CDCl3) δ 164.85, 161.14, 158.88, 142.81, 138.71, 136.77, 129.16, 128.59, 128.26, 75.91, 72.83, 70.50, 31.90, 29.77, 29.22, 29.55, 29.45, 29.41, 28.44, 28.19, 19.00.

Workup

  1. stirringThe reaction mixture was then stirred
  2. temperatureat reflux under argon atmosphere overnight
  3. stirringthe reaction mixture was stirred overnight
  4. temperatureat reflux under argon atmosphere
  5. extractionThe mixture was extracted with two portions of 70 mL of dichloromethane
  6. washThe combined organic solution was washed with a portion of 70 mL 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. washElution with acetone-hexanes 2:1

Sources & evidence

ORD record
ord-328517402a954e9bab0b1e747dcd64db
Source dataset
uspto-grants-2015_02
Patent number
US08952025B2

Reaction notes

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