Cesium carbonate → Methyl 4-((6-(methylamino)pyrimidin-4-yl)amino)-3-nitrobenzoate

HRID 58183

반응식

HRID 58183 반응식
Cl[C:2]1[N:7]=[CH:6][N:5]=[C:4]([NH:8][CH3:9])[CH:3]=1.[NH2:10][C:11]1[CH:20]=[CH:19][C:14]([C:15]([O:17][CH3:18])=[O:16])=[CH:13][C:12]=1[N+:21]([O-:23])=[O:22].C([O-])([O-])=O.[Cs+].[Cs+].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>C1(C)C=CC=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.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd]>[CH3:9][NH:8][C:4]1[N:5]=[CH:6][N:7]=[C:2]([NH:10][C:11]2[CH:20]=[CH:19][C:14]([C:15]([O:17][CH3:18])=[O:16])=[CH:13][C:12]=2[N+:21]([O-:23])=[O:22])[CH:3]=1

참가 물질

7

반응물 4

HCID 10796Cesium carbonateHCID 3094796-chloro-N-methylpyrimidin-4-amineHCID 6360441,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine)HCID 3941008Methyl 4-amino-3-nitrobenzoate

생성물 1

HCID 118026274Methyl 4-((6-(methylamino)pyrimidin-4-yl)amino)-3-nitrobenzoate수율 51%

시약·촉매·용매 2

HCID 9811564Bis(dibenzylideneacetone)palladium촉매HCID 1140Toluene용매

반응 조건

온도
110 °C

실험 절차

6-chloro-N-methylpyrimidin-4-amine, 3 (3 g, 20.97 mmol) and methyl 4-amino-3-nitrobenzoate (3.9 g, 20.97 mmol) were taken in toluene (5 mL) in a seal tube under Argon atmosphere at room temperature. The Argon gas was purged for 5-10 min. Then Cs2CO3 (17.0 g, 52.4 mmol) and Xantphos (3.6 g, 6.29 mmol) were added and the resulting reaction mixture was purged with argon gas for 5 min, followed by Pd2(dba)3 (3.8 g, 4.19 mmol) was added. The argon gas purging was continued for additional 5 min before sealing the reaction vial. Then the reaction mixture was heated at 110° C. for 16 h. After completion of the reaction by TLC, the reaction mixture was cooled to rt, filtered through celite bed and the filtrate was evaporated under vacuum to get a crude residue. The crude residue was purified by column chromatography on silica gel to afford the title compound (3.2 g, yield: 51%) as a solid; MS (ESI): 304.2 [M+H]+.

후처리

  1. customThe Argon gas was purged for 5-10 min
  2. customthe resulting reaction mixture
  3. customwas purged with argon gas for 5 min
  4. additionwas added
  5. customThe argon gas purging
  6. customAfter completion of the reaction by TLC
  7. temperaturethe reaction mixture was cooled to rt
  8. filtrationfiltered through celite bed
  9. customthe filtrate was evaporated under vacuum
  10. customto get a crude residue
  11. customThe crude residue was purified by column chromatography on silica gel

출처 및 근거

ORD 기록
ord-19b51ba8cea940ed9faef692ecfb7551
출처 데이터셋
uspto-grants-2016_09
특허 번호
US09434697B2

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