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

HRID 68303

반응식

HRID 68303 반응식
[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

참가 물질

6

반응물 4

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

생성물 1

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

시약·촉매·용매 1

HCID 18463208dimethoxyethane N,N-dimethylformamide용매

반응 조건

온도
75 °C

실험 절차

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 The vial was sealed, withdrawn from the glove box, and agitated in an incubator shaker at 75° C. for 16 hours.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.

후처리

  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)

출처 및 근거

ORD 기록
ord-92d88e080b0e411eb78625e6bd72b495
출처 데이터셋
uspto-grants-2014_09
특허 번호
US08822451B2

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