Cesium carbonate → HCID 67128909, 화합물

HRID 449901

반응식

HRID 449901 반응식
[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

참가 물질

7

반응물 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

생성물 1

HCID 67128909HCID 67128909, 화합물수율 23.2%

시약·촉매·용매 2

HCID 9811564Bis(dibenzylideneacetone)palladium촉매HCID 312751,4-Dioxane용매

반응 조건

온도
110 °C

실험 절차

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+].

후처리

  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)

출처 및 근거

ORD 기록
ord-761d0ebbebfe4858934c252f17f95520
출처 데이터셋
uspto-grants-2013_07
특허 번호
US08486950B2

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