Water → HCID 178432729, compound

HRID 241006Notes

Reaction equation

HRID 241006 reaction equation
Cl.[C:2]([NH2:5])(=[NH:4])[CH3:3].C[O-].[Na+].[F:9][C:10]1[CH:24]=[CH:23][C:13]([CH2:14][CH:15]([C:20](=O)[CH3:21])[C:16](OC)=[O:17])=[CH:12][CH:11]=1.O>CO>[F:9][C:10]1[CH:11]=[CH:12][C:13]([CH2:14][C:15]2[C:16]([OH:17])=[N:4][C:2]([CH3:3])=[N:5][C:20]=2[CH3:21])=[CH:23][CH:24]=1

Participants

6

Reactant 4

HCID 962WaterHCID 67170Acetamidine monohydrochlorideHCID 2758966HCID 2758966, compoundHCID 10942334Sodium Methoxide

Product 1

HCID 178432729HCID 178432729, compoundYield 89.2%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent3×

Procedure

To a suspension of acetamidine hydrochloride (0.54 g, 5.71 mmol) in methanol (8 mL) was added a 30% solution of sodium methoxide in methanol (1.1 mL, 5.7 mmol), and the resulting solution was stirred at room temperature for 45 min. Then, a solution of methyl 2-(4-fluorobenzyl)-3-oxobutanoate (0.80 g, 3.57 mmol) in methanol (3 mL) was added dropwise, and the resulting mixture was stirred at room temperature for 22 h. Water (100 mL) was added, and the mixture was extracted with chloroform (4×50 mL). The combined organic extracts were dried over sodium sulfate, filtered and concentrated to provide 5-(4-fluorobenzyl)-2,6-dimethylpyrimidin-4-ol (0.74 g, 89% yield) as a colorless solid. 1H NMR (400 MHz, methanol-d4): 7.21 (m, 2H), 6.96 (m, 2H), 3.84 (s, 2H), 2.35 (s, 3H), 2.25 (s, 3H); MS (EI) for C13H13FN2O: 233 (MH+).

Workup

  1. stirringthe resulting mixture was stirred at room temperature for 22 h
  2. extractionthe mixture was extracted with chloroform (4×50 mL)
  3. dry with materialThe combined organic extracts were dried over sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-610f8a0d391f4b18be02d9f52560a9fe
Source dataset
uspto-grants-2014_02
Patent number
US08648066B2

Reaction notes

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