Oxygen → 6-(2,6-Dimethoxy-phenyl)-2-methylsulfanyl-pyrimidine-4-carboxylic acid amide

HRID 68303

反応式

HRID 68303 の反応式
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][CH:6]=[C:5]([O:9][CH3:10])[C:4]=1B(O)O.O=O.Cl[C:17]1[N:22]=[C:21]([S:23][CH3:24])[N:20]=[C:19]([C:25]([NH2:27])=[O:26])[CH:18]=1.P([O-])([O-])([O-])=O.[K+].[K+].[K+]>CN(C=O)C.COCCOC>[CH3:1][O:2][C:3]1[CH:8]=[CH:7][CH:6]=[C:5]([O:9][CH3:10])[C:4]=1[C:17]1[N:22]=[C:21]([S:23][CH3:24])[N:20]=[C:19]([C:25]([NH2:27])=[O:26])[CH:18]=1

参加物

6

反応物 4

HCID 977OxygenHCID 62657Potassium Phosphate, TribasicHCID 2392766-Chloro-2-methylsulfanylpyrimidine-4-carboxamideHCID 2734343(2,6-Dimethoxyphenyl)boronic acid

生成物 1

HCID 588727556-(2,6-Dimethoxy-phenyl)-2-methylsulfanyl-pyrimidine-4-carboxylic acid amide

試薬・触媒・溶媒 1

HCID 18463208dimethoxyethane N,N-dimethylformamide溶媒

反応条件

温度
75 °C

実験手順

A 7 mL teflon-faced screw-cap vial was charged with 2,6-dimethoxyphenyl-boronic acid (218 mg, 1.2 mmol, 2 eq.) and dichloro-bis-(diphenylphosphinoferrocene)-palladium-dichloromethane adduct (49 mg, 60 μmol, 10 mol %). In a glove box under a nitrogen atmosphere (O2 content<=0.5%), the vial was charged with a solution of the 6-chloro-2-methylsulfanyl-pyrimidine-4-carboxylic acid amide (122 mg, 0.6 mmol) in degassed DMF/DME (1/1, 4.5 mL), and a degassed aqueous 1 M solution of potassium phosphate (1.0 mL, 1 mmol, 1.7 eq.). The vial was sealed, withdrawn from the glove box, and agitated in an incubator shaker at 75° C. for 16 hours. The cooled mixture was then diluted with chloroform (15 mL), and washed with brine (20 mL, 2×10 mL), and aqueous 1 M potassium carbonate (10 mL). The organic layer (solution of 6-(2,6-dimethoxy-phenyl)-2-methylsulfanyl-pyrimidine-4-carboxylic acid amide in chloroform) was then used directly in the next step.

後処理

  1. customThe vial was sealed
  2. customwithdrawn from the glove box
  3. additionThe cooled mixture was then diluted with chloroform (15 mL)
  4. washwashed with brine (20 mL, 2×10 mL), and aqueous 1 M potassium carbonate (10 mL)

出典と根拠

ORDレコード
ord-92d88e080b0e411eb78625e6bd72b495
出典データセット
uspto-grants-2014_09
特許番号
US08822451B2

関連ノート

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