Cesium carbonate → HCID 67128909、化合物

HRID 449901

反応式

HRID 449901 の反応式
[NH2:1][C:2]1[C:7]([N+:8]([O-:10])=[O:9])=[CH:6][N:5]=[C:4](Cl)[CH:3]=1.[NH2:12][C:13]1[CH:18]=[C:17]([CH3:19])[N:16]=[C:15]([CH3:20])[N:14]=1.CC1(C)C2C(=C(P(C3C=CC=CC=3)C3C=CC=CC=3)C=CC=2)OC2C(P(C3C=CC=CC=3)C3C=CC=CC=3)=CC=CC1=2.C([O-])([O-])=O.[Cs+].[Cs+]>C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd].O1CCOCC1>[CH3:20][C:15]1[N:14]=[C:13]([NH:12][C:4]2[CH:3]=[C:2]([NH2:1])[C:7]([N+:8]([O-:10])=[O:9])=[CH:6][N:5]=2)[CH:18]=[C:17]([CH3:19])[N:16]=1

参加物

7

反応物 4

HCID 10796Cesium carbonateHCID 680392,6-Dimethyl-4-aminopyrimidineHCID 6360441,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine)HCID 109100582-chloro-5-nitropyridin-4-amine

生成物 1

HCID 67128909HCID 67128909、化合物収率 23.2%

試薬・触媒・溶媒 2

HCID 9811564Bis(dibenzylideneacetone)palladium触媒HCID 312751,4-Dioxane溶媒

反応条件

温度
110 °C

実験手順

To a 200 ml flask was added 4-amino-2-chloro-5-nitropyridine (1.00 g, 5.76 mmol), 4-amino-2,6-dimethylpyrimidine (1.42 g, 11.5 mmol), Pd2(dba)3 (0.528 g, 0.576 mmol), XantPhos (0.400 g, 0.691 mmol), Cs2CO3 (4.13 g, 12.7 mmol) and dioxane (45 mL). The mixture was degassed with N2 for 2 min and then heated at 110° C. for 16 hrs. After cooling to room temperature the reaction was filtered and concentrated under reduced pressure. The residue was purified by column chromatography on silica gel (0-10% methanol/dichloromethane) to give N-(2,6-dimethylpyrimidin-4-yl)-5-nitropyridine-2,4-diamine (0.348 g, yield: 23%). LCMS (ESI) m/z: 261.2 [M+H+].

後処理

  1. customThe mixture was degassed with N2 for 2 min
  2. temperatureAfter cooling to room temperature the reaction
  3. filtrationwas filtered
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was purified by column chromatography on silica gel (0-10% methanol/dichloromethane)

出典と根拠

ORDレコード
ord-761d0ebbebfe4858934c252f17f95520
出典データセット
uspto-grants-2013_07
特許番号
US08486950B2

関連ノート

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