Hydrochloric Acid → 6-[2-(2-methoxy-ethoxy)-phenyl]-2-methyl-3H-pyrimidin-4-one

HRID 1891010Notes

Reaction equation

HRID 1891010 reaction equation
C(O[C:4](=[O:19])[CH2:5][C:6]([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=1[O:14][CH2:15][CH2:16][O:17][CH3:18])=O)C.Cl.[C:21]([NH2:24])(=[NH:23])[CH3:22].C(O[K])(C)(C)C.Cl>C(O)C.O>[CH3:18][O:17][CH2:16][CH2:15][O:14][C:9]1[CH:10]=[CH:11][CH:12]=[CH:13][C:8]=1[C:6]1[N:23]=[C:21]([CH3:22])[NH:24][C:4](=[O:19])[CH:5]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 67170Acetamidine monohydrochlorideHCID 585505203-[2-(2-Methoxy-ethoxy)-phenyl]-3-oxo-propionic acid ethyl esterHCID 178418922HCID 178418922, compound

Product 1

HCID 1361275746-[2-(2-methoxy-ethoxy)-phenyl]-2-methyl-3H-pyrimidin-4-oneYield 67%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

To a solution of 3-[2-(2-methoxy-ethoxy)-phenyl]-3-oxo-propionic acid ethyl ester (0.26 g, 0.98 mmol) in absolute ethanol (10 mL) was added acetamidine hydrochloride (0.3 g, 3.19 mmol) and tBuOK (0.5 g, 4.46 mmol). The reaction mixture refluxed 12 h. After cooling, a mixture poured into water (10 mL), adjusted to pH 3 with 10% HCl and extracted with CHCl3 (3×20 mL). Organic layers were combined, washed with water (10 mL), then dried over anhydrous sodium sulfate, concentrated and triturated with hexane to obtained 0.17 g (67%) 6-[2-(2-methoxy-ethoxy)-phenyl]-2-methyl-3H-pyrimidin-4-one as a white powder.

Workup

  1. temperatureThe reaction mixture refluxed 12 h
  2. temperatureAfter cooling
  3. extractionextracted with CHCl3 (3×20 mL)
  4. washwashed with water (10 mL)
  5. dry with materialdried over anhydrous sodium sulfate
  6. concentrationconcentrated
  7. customtriturated with hexane

Sources & evidence

ORD record
ord-1f799b78f4b544bd851c4fac63e8462d
Source dataset
uspto-grants-2013_08
Patent number
US08507498B2

Reaction notes

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