Pyridine → 1-(2-Methoxyethyl)-6-(pyridin-2-yl)-2-thioxo-2,3-dihydropyrimidin-4(1H)-one

HRID 77550Notes

Reaction equation

HRID 77550 reaction equation
[CH3:1][O:2][CH2:3][CH2:4][N:5]1[C:10]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][N:12]=2)=[CH:9][C:8](=[O:17])[N:7]=[C:6]1[S:18]C.[NH4+]=S.N1C=CC=CC=1.[OH-].[Na+]>O1CCOCC1.O>[CH3:1][O:2][CH2:3][CH2:4][N:5]1[C:10]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][N:12]=2)=[CH:9][C:8](=[O:17])[NH:7][C:6]1=[S:18]

Participants

6

Reactant 3

HCID 1049PyridineHCID 14798Sodium HydroxideHCID 86684690HCID 86684690, compound

Product 1

HCID 866846891-(2-Methoxyethyl)-6-(pyridin-2-yl)-2-thioxo-2,3-dihydropyrimidin-4(1H)-oneYield 3.2%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 312751,4-DioxaneSolvent

Procedure

A mixture of crude 1-(2-methoxyethyl)-2-(methylthio)-6-(pyridin-2-yl)pyrimidin-4(1H)-one (100 mg, 0.36 mmol), ammonium sulfide solution (0.2 mL, 0.64 mmol) and pyridine (0.2 mL) was stirred in dioxane (2 mL) at 70° C. for 4 hours. The reaction mixture was diluted with water (10 mL), basified with 2M NaOH and washed with dichloromethane (3×10 mL). The aqueous layer was acidified to pH 6 with 2M HCl and extracted with ethyl acetate (3×10 mL). The combined organic layers were washed with water (3×10 mL), brine (3×10 mL), dried over MgSO4 and concentrated in vacuo. The crude material was purified by mass directed automatic purification using an acidic method to give the product as a brown solid (3 mg, 3%).

Workup

  1. washwashed with dichloromethane (3×10 mL)
  2. extractionextracted with ethyl acetate (3×10 mL)
  3. washThe combined organic layers were washed with water (3×10 mL), brine (3×10 mL)
  4. dry with materialdried over MgSO4
  5. concentrationconcentrated in vacuo
  6. customThe crude material was purified by mass
  7. custompurification

Sources & evidence

ORD record
ord-43ec51ac7ece453d8861e5713735167b
Source dataset
uspto-grants-2014_09
Patent number
US08841314B2

Reaction notes

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