Cesium carbonate → tert-butyl 5-((5-chloro-2-((1-methyl-1H-imidazol-4-yl)amino)pyrimidin-4-yl)amino)hexahvdrocyclopenta[c]pyrrole-2(1H)-carboxylate

HRID 1478045ノート

反応式

HRID 1478045 の反応式
Cl[C:2]1[N:7]=[C:6]([NH:8][CH:9]2[CH2:23][CH:12]3[CH2:13][N:14]([C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])[CH2:15][CH:11]3[CH2:10]2)[C:5]([Cl:24])=[CH:4][N:3]=1.[CH3:25][N:26]1[CH:30]=[C:29]([NH2:31])[N:28]=[CH:27]1.C1C=CC(P(C2C(C3C(P(C4C=CC=CC=4)C4C=CC=CC=4)=CC=C4C=3C=CC=C4)=C3C(C=CC=C3)=CC=2)C2C=CC=CC=2)=CC=1.C([O-])([O-])=O.[Cs+].[Cs+]>O1CCOCC1.CC([O-])=O.CC([O-])=O.[Pd+2]>[Cl:24][C:5]1[C:6]([NH:8][CH:9]2[CH2:23][CH:12]3[CH2:13][N:14]([C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])[CH2:15][CH:11]3[CH2:10]2)=[N:7][C:2]([NH:31][C:29]2[N:28]=[CH:27][N:26]([CH3:25])[CH:30]=2)=[N:3][CH:4]=1

参加物

7

反応物 4

HCID 10796Cesium carbonateHCID 634876Binap, (A+-)-HCID 108986491-Methyl-1H-imidazol-4-amineHCID 118389983tert-butyl 5-((2,5-dichloropyrimidin-4-yl)amino)hexahydrocyclopenta[c]pyrrole-2(1H)-carboxylate

生成物 1

HCID 118390059tert-butyl 5-((5-chloro-2-((1-methyl-1H-imidazol-4-yl)amino)pyrimidin-4-yl)amino)hexahvdrocyclopenta[c]pyrrole-2(1H)-carboxylate収率 48.4%

試薬・触媒・溶媒 2

HCID 167845palladium(II) acetate触媒HCID 312751,4-Dioxane溶媒

反応条件

温度
150 °C

実験手順

To a suspension of tert-butyl 5-[(2,5-dichloropyrimidin-4-yl)amino]-hexahydrocyclopenta[c]pyrrole-2(1H)-carboxylate (373.0 mg, 1.00 mmol) and 1-methylimidazol-4-amine (341.8 mg, 3.52 mmol) in dioxane (10 mL) were added Pd(OAc)2 (52.0 mg, 0.23 mmol), BINAP (125.0 mg, 0.19 mmol) and Cs2CO3 (647.2 mg, 1.99 mmol). The reaction mixture was stirred at 150° C. under microwave for 2 h and concentrated in vacuo. The residue was purified by silica gel column chromatography (MeOH/DCM (v/v)=1/50) to give the title compound as a pale yellow solid (0.21 g, 48%).

後処理

  1. concentrationconcentrated in vacuo
  2. customThe residue was purified by silica gel column chromatography (MeOH/DCM (v/v)=1/50)

出典と根拠

ORDレコード
ord-003bd9714fbe43df9572207a0da3282d
出典データセット
uspto-grants-2016_08
特許番号
US09403801B2

反応ノート

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