Sulfuric Acid → 2-(6-((2-(3-Chlorophenyl)-6-ethylpyrimidin-4-yl)oxy)pyridin-3-yl)acetamide

HRID 1508872Notes

Reaction equation

HRID 1508872 reaction equation
S(=O)(=O)(O)[OH:2].[Cl:6][C:7]1[CH:8]=[C:9]([C:13]2[N:18]=[C:17]([O:19][C:20]3[N:25]=[CH:24][C:23]([CH2:26][C:27]#[N:28])=[CH:22][CH:21]=3)[CH:16]=[C:15]([CH2:29][CH3:30])[N:14]=2)[CH:10]=[CH:11][CH:12]=1>C(=O)(O)[O-].[Na+]>[Cl:6][C:7]1[CH:8]=[C:9]([C:13]2[N:18]=[C:17]([O:19][C:20]3[N:25]=[CH:24][C:23]([CH2:26][C:27]([NH2:28])=[O:2])=[CH:22][CH:21]=3)[CH:16]=[C:15]([CH2:29][CH3:30])[N:14]=2)[CH:10]=[CH:11][CH:12]=1

Participants

4

Reactant 2

HCID 1118Sulfuric AcidHCID 90111123HCID 90111123, compound

Product 1

HCID 901093772-(6-((2-(3-Chlorophenyl)-6-ethylpyrimidin-4-yl)oxy)pyridin-3-yl)acetamideYield 34%

Reagents, catalysts & solvents 1

HCID 516892Sodium BicarbonateSolvent

Procedure

Sulfuric acid (2 mL) was added to 2-(6-((2-(3-chlorophenyl)-6-ethylpyrimidin-4-yl)oxy)pyridin-3-yl)acetonitrile (0.061 g, 0.18 mmol) at 0° C. and slowly warmed to rt. The mixture was stirred for 2 h, diluted with saturated aqueous sodium bicarbonate, and extracted with ethyl acetate. The combined organic layer was dried over anhydrous sodium sulfate, filtered, and the filtrate was concentrated. The residue was purified by column chromatography (silica, dichloromethane/methanol) to afford the title compound (0.020 g, 34%) as a white solid. MW=368.22. 1H NMR (DMSO-d6, 300 MHz) δ 8.44-8.37 (m, 2H), 8.10-8.05 (m, 1H), 7.92 (s, 1H), 7.70-7.56 (m, 2H), 7.53-7.43 (m, 2H), 7.01 (s, 1H), 6.55 (d, J=9.4 Hz, 1H), 3.30 (d, 2H), 2.93 (q, J=7.6 Hz, 2H), 1.33 (t, J=7.6 Hz, 3H); APCI MS m/z 369 [M+H]+.

Workup

  1. extractionextracted with ethyl acetate
  2. dry with materialThe combined organic layer was dried over anhydrous sodium sulfate
  3. filtrationfiltered
  4. concentrationthe filtrate was concentrated
  5. customThe residue was purified by column chromatography (silica, dichloromethane/methanol)

Sources & evidence

ORD record
ord-b89de6c8223e48aa89f24b1e4a91e16a
Source dataset
uspto-grants-2015_12
Patent number
US09221843B2

Reaction notes

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