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

HRID 58183

反応式

HRID 58183 の反応式
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

参加物

7

反応物 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

生成物 1

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

試薬・触媒・溶媒 2

HCID 9811564Bis(dibenzylideneacetone)palladium触媒HCID 1140Toluene溶媒

反応条件

温度
110 °C

実験手順

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]+.

後処理

  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

出典と根拠

ORDレコード
ord-19b51ba8cea940ed9faef692ecfb7551
出典データセット
uspto-grants-2016_09
特許番号
US09434697B2

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