Sulfuric Acid → 3-[3-(2-Methyl-pyrimidin-4-yl)-phenyl]-3-oxo-propionic acid tert-butyl ester

HRID 498242Notes

Reaction equation

HRID 498242 reaction equation
CO[C:3](=[O:17])[C:4]1[CH:9]=[CH:8][CH:7]=[C:6]([C:10]2[CH:15]=[CH:14][N:13]=[C:12]([CH3:16])[N:11]=2)[CH:5]=1.[C:18]([C:21]1[CH:22]=C(C=C[CH:29]=1)C(O)=O)(=O)C.C(NC(N[C:40](=[O:42])[CH3:41])NC(=O)C)(=O)C.[OH:43]S(O)(=O)=O>O>[C:21]([O:43][C:40](=[O:42])[CH2:41][C:3]([C:4]1[CH:9]=[CH:8][CH:7]=[C:6]([C:10]2[CH:15]=[CH:14][N:13]=[C:12]([CH3:16])[N:11]=2)[CH:5]=1)=[O:17])([CH3:22])([CH3:29])[CH3:18]

Participants

6

Reactant 4

HCID 1118Sulfuric AcidHCID 2203243-Acetylbenzoic acidHCID 536854N-(Bis-acetylamino-methyl)-acetamideHCID 17174862Methyl 3-(2-methylpyrimidin-4-yl)benzoate

Product 1

HCID 694867223-[3-(2-Methyl-pyrimidin-4-yl)-phenyl]-3-oxo-propionic acid tert-butyl ester

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
155 °C

Procedure

The title compound was prepared from 3-(2-methyl-pyrimidin-4-yl)-benzoic acid methyl ester [prepared by the following procedure: A mixture of 3-acetyl-benzoic acid (0.82 g, 5 mmol), N-(bis-acetylamino-methyl)-acetamide (0.94 g, 5 mmol) and conc. H2SO4 (0.01 ml) was heated to 155° C. for 6 h. The cooled mixture was diluted with H2O (20 ml) and the precipitate was collected, dried and esterified by heating in MeOH (12 ml)/4N HCl-Et2O (3 ml) for 20 h at 40° C.; white crystals (0.27 g).] (0.80 g, 3.5 mmol by treatment with lithium tert-butyl acetate according to general procedure K (method b). Obtained as a yellow solid (1.36 g, crude product).

Workup

  1. customprepared by the following procedure
  2. customthe precipitate was collected
  3. customdried
  4. temperatureby heating in MeOH (12 ml)/4N HCl-Et2O (3 ml) for 20 h at 40° C.
  5. customObtained as a yellow solid (1.36 g, crude product)

Sources & evidence

ORD record
ord-9acf5ee7dc8247b589bee8b4fb99d2a0
Source dataset
uspto-grants-2005_09
Patent number
US06949542B2

Reaction notes

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