Potassium Carbonate → 2-(5-Cyano-2-{[(2,4-dimethoxyphenyl)methyl]amino}anilino)-5-nitropyrimidin-4-yl thiocyanate

HRID 605856노트

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HRID 605856 반응식
[CH3:1][O:2][C:3]1[CH:19]=[C:18]([O:20][CH3:21])[CH:17]=[CH:16][C:4]=1[CH2:5][NH:6][C:7]1[CH:14]=[CH:13][C:10]([C:11]#[N:12])=[CH:9][C:8]=1[NH2:15].C(=O)([O-])[O-].[K+].[K+].Cl[C:29]1[N:34]=[C:33]([S:35][C:36]#[N:37])[C:32]([N+:38]([O-:40])=[O:39])=[CH:31][N:30]=1>C(#N)C>[CH3:1][O:2][C:3]1[CH:19]=[C:18]([O:20][CH3:21])[CH:17]=[CH:16][C:4]=1[CH2:5][NH:6][C:7]1[CH:14]=[CH:13][C:10]([C:11]#[N:12])=[CH:9][C:8]=1[NH:15][C:29]1[N:34]=[C:33]([S:35][C:36]#[N:37])[C:32]([N+:38]([O-:40])=[O:39])=[CH:31][N:30]=1

참가 물질

5

반응물 3

HCID 11430Potassium CarbonateHCID 210775882-Chloro-5-nitropyrimidin-4-yl thiocyanateHCID 566052433-Amino-4-{[(2,4-dimethoxyphenyl)methyl]amino}benzonitrile

생성물 1

HCID 566052112-(5-Cyano-2-{[(2,4-dimethoxyphenyl)methyl]amino}anilino)-5-nitropyrimidin-4-yl thiocyanate수율 6.5%

시약·촉매·용매 1

HCID 6342Acetonitrile용매2회

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온도
0 °C

실험 절차

A solution of 4-(2,4-dimethoxybenzylamino)-3-aminobenzonitrile (3.9 g) in acetonitrile (100 mL) was cooled to 0° C. and treated with potassium carbonate (6.3 g) followed by a solution containing 3 g of 2-chloro-5-nitro-4-thiocyanatopyrimidine (WO 2003/032994) in acetonitrile (50 mL). The mixture was stirred for 30 minutes at 0° C. and 30 minutes at room temperature resulting in the formation of a precipitate. The mixture was quenched at 0° C. by the addition of 4% acetic acid (150 mL) and filtered. The precipitate was swirled in 100 mL acetonitrile and filtered again. The precipitate was washed with acetonitrile, which resulted in the slow dissolution of product into the filtrate. After air-drying, 1.5 g of the title compound remained as the precipitate cake. The filtrate was extracted with EtOAc, dried over Na2SO4, filtered, and concentrated in vacuo. Column chromatography (0→20% EtOAc/DCM) and recrystallization from acetonitrile provided 0.415 g of additional title compound.

후처리

  1. customresulting in the formation of a precipitate
  2. customThe mixture was quenched at 0° C. by the addition of 4% acetic acid (150 mL)
  3. filtrationfiltered
  4. filtrationfiltered again
  5. washThe precipitate was washed with acetonitrile, which
  6. customresulted in the slow dissolution of product into the filtrate
  7. customAfter air-drying
  8. extractionThe filtrate was extracted with EtOAc
  9. dry with materialdried over Na2SO4
  10. filtrationfiltered
  11. concentrationconcentrated in vacuo
  12. customColumn chromatography (0→20% EtOAc/DCM) and recrystallization from acetonitrile

출처 및 근거

ORD 기록
ord-c4ecd725c5864c9fa20fa16dcb1d58ab
출처 데이터셋
uspto-grants-2011_03
특허 번호
US07915268B2

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