Sodium hydride → Methyl 4-(4-fluorophenyl)-6-(1-methylethyl)-2-(methyl(methylsulfonyl)amino)-5-pyrimidinecarboxylate

HRID 1369963

Reaction equation

HRID 1369963 reaction equation
[NH2:1][C:2](=[C:10]([C:15](=O)[CH:16]([CH3:18])[CH3:17])[C:11]([O:13][CH3:14])=[O:12])[C:3]1[CH:8]=[CH:7][C:6]([F:9])=[CH:5][CH:4]=1.CN(C)C(=O)C.[C:26]([N:28]([CH3:33])[S:29]([CH3:32])(=[O:31])=[O:30])#[N:27].[H-].[Na+]>O>[F:9][C:6]1[CH:7]=[CH:8][C:3]([C:2]2[C:10]([C:11]([O:13][CH3:14])=[O:12])=[C:15]([CH:16]([CH3:18])[CH3:17])[N:27]=[C:26]([N:28]([S:29]([CH3:32])(=[O:31])=[O:30])[CH3:33])[N:1]=2)=[CH:4][CH:5]=1

Participants

6

Reactant 4

HCID 24758Sodium hydrideHCID 31374DimethylacetamideHCID 10219456N-cyano-N-methylmethanesulphonamideHCID 178500902HCID 178500902, compound

Product 1

HCID 9929821Methyl 4-(4-fluorophenyl)-6-(1-methylethyl)-2-(methyl(methylsulfonyl)amino)-5-pyrimidinecarboxylateYield 29.1%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

2.66 g (10.0 mmol) of methyl 2-[1-amino-1-(4-fluorophenyl)methylene]-4-methyl-3-oxopentanoate were introduced into 12 g of N,N-dimethylacetamide together with 2.70 g (20.0 mmol) of N-cyano-N-methylmethanesulphonamide. 440 mg (11.0 mmol) of sodium hydride (60% in oil) were added to this solution at room temperature over the course of 2 h. An orange-red clear solution was obtained. After 6 h at room temperature, the reaction solution was poured onto 25 ml of water. The suspension was stirred in an ice bath for 30 minutes, and the precipitate was filtered off and washed with water (2×10 ml). After drying in a high vacuum, 1.11 g (29.1%) of methyl 4-(4-fluorophenyl)-6-isopropyl-2-(N-methanesulphonyl-N-methylamino)pyrimidine-5-carboxylate were obtained in the form of a pale beige solid. The product still contained traces of methyl 2-[1-amino-1-(4-fluorophenyl)methylene]-4-methyl-3-oxopentanoate.

Workup

  1. customAn orange-red clear solution was obtained
  2. filtrationthe precipitate was filtered off
  3. washwashed with water (2×10 ml)
  4. customAfter drying in a high vacuum

Sources & evidence

ORD record
ord-ba404f0fb2204f88a6df4bb4afb1b514
Source dataset
uspto-grants-2003_06
Patent number
US06579984B1

Linked notes

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