Cesium carbonate → 2-Methylthio-4-chloro-5-nitro-6-(3-dimethylaminocarbonylphenoxy)pyrimidine

HRID 1456941

Reaction equation

HRID 1456941 reaction equation
[CH3:1][S:2][C:3]1[N:8]=[C:7](Cl)[C:6]([N+:10]([O-:12])=[O:11])=[C:5]([Cl:13])[N:4]=1.C(=O)([O-])[O-].[Cs+].[Cs+].[CH3:20][N:21]([CH3:31])[C:22]([C:24]1[CH:25]=[C:26]([OH:30])[CH:27]=[CH:28][CH:29]=1)=[O:23]>C(#N)C>[CH3:1][S:2][C:3]1[N:4]=[C:5]([Cl:13])[C:6]([N+:10]([O-:12])=[O:11])=[C:7]([O:30][C:26]2[CH:27]=[CH:28][CH:29]=[C:24]([C:22]([N:21]([CH3:31])[CH3:20])=[O:23])[CH:25]=2)[N:8]=1

Participants

5

Reactant 3

HCID 10796Cesium carbonateHCID 6375243-hydroxy-N,N-dimethylbenzamideHCID 113454584,6-Dichloro-2-(methylthio)-5-nitropyrimidine

Product 1

HCID 221026862-Methylthio-4-chloro-5-nitro-6-(3-dimethylaminocarbonylphenoxy)pyrimidineYield 83%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To 2-methylthio-4,6-dichloro-5-nitropyrimidine, a compound of formula (A), (5.0 g, 20.8 mmol) in 200 mL acetonitrile at 0° C. was added cesium carbonate (8.82 g, 27.1 mmol) followed by the addition of 3-(dimethylaminocarbonyl)phenol (3.44 g, 20.8 mmol), a compound of formula (B), and the reaction mixture was stirred for 16 hours. The volatiles were evaporated and the residue chromatographed on silica gel (CH2 Cl2 /ethyl acetate, 7:12) to afford 6.3 g (83% yield) of 2-methylthio-4-chloro-5-nitro-6-(3-(dimethylaminocarbonyl)phenoxy)pyrimidine, a compound of formula (C).

Workup

  1. customThe volatiles were evaporated
  2. customthe residue chromatographed on silica gel (CH2 Cl2 /ethyl acetate, 7:12)

Sources & evidence

ORD record
ord-56de6141aa3f4eaf9e6317b0a41d0202
Source dataset
uspto-grants-1998_12
Patent number
US05846970

Linked notes

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