Water → 5-Pyrimidinecarboxylic acid, 4-formyl-6-(methylthio)-2-phenyl-, ethyl ester

HRID 1049961Notes

Reaction equation

HRID 1049961 reaction equation
[CH3:1][C:2]1[C:7]([C:8]([O:10][CH2:11][CH3:12])=[O:9])=[C:6]([S:13][CH3:14])[N:5]=[C:4]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[N:3]=1.[Se](=O)=[O:22].O>O1CCOCC1>[CH:1]([C:2]1[C:7]([C:8]([O:10][CH2:11][CH3:12])=[O:9])=[C:6]([S:13][CH3:14])[N:5]=[C:4]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[N:3]=1)=[O:22]

Participants

5

Reactant 3

HCID 962WaterHCID 24007Selenium DioxideHCID 35177757HCID 35177757, compound

Product 1

HCID 866770205-Pyrimidinecarboxylic acid, 4-formyl-6-(methylthio)-2-phenyl-, ethyl esterYield 58.9%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

To a solution of ethyl 4-methyl-6-(methylthio)-2-phenylpyrimidine-5-carboxylate (5 g 17.4 mmol) in 1.4-dioxane (50 mL) was added selenium dioxide (9.6 g, 86.5 mmol) and water (1.5 mL) and the reaction mixture was refluxed for 12 hours. Dioxane was removed in a vacuum and the crude solid suspended in ethyl acetate and filtered. The filtrate was concentrated and purified by column chromatography over silica gel using 10% ethyl acetate in petroleum ether as eluent to give the desired product (3.1 g). 1H-NMR (400 Hz, CDCl3): δ 10.10 (s, 1H), 8.54 (d, J=7.2 Hz, 2H), 7.56-7.43 (m, 3H), 4.47 (q, J=7.2 Hz, 2H), 2.67 (s, 3H), 2.64 (s, 3H), 1.42 (t, J=7.2 Hz, 3H); MS m/z 303.1 (M+1).

Workup

  1. temperaturethe reaction mixture was refluxed for 12 hours
  2. customDioxane was removed in a vacuum
  3. filtrationfiltered
  4. concentrationThe filtrate was concentrated
  5. custompurified by column chromatography over silica gel using 10% ethyl acetate in petroleum ether as eluent

Sources & evidence

ORD record
ord-e65c57e0445d4adda53ee142de8bcd63
Source dataset
uspto-grants-2016_07
Patent number
US09382277B2

Reaction notes

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