Cesium carbonate → 5-{1-tert-Butyl-2-[2-(2,4-dimethyl-oxazol-5-yl)-phenyl]-1H-benzimidazol-5-yl}-pyrimidin-2-ylamine

HRID 1966752

反応式

HRID 1966752 の反応式
[C:1]([N:5]1[C:9]2[CH:10]=[CH:11][C:12]([C:14]3[CH:15]=[N:16][C:17]([NH2:20])=[N:18][CH:19]=3)=[CH:13][C:8]=2[N:7]=[C:6]1[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][C:22]=1I)([CH3:4])([CH3:3])[CH3:2].[CH3:28][C:29]1[O:30][CH:31]=[C:32]([CH3:34])[N:33]=1.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C([O-])([O-])=O.[Cs+].[Cs+]>CN(C=O)C.CCOC(C)=O.O.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[C:1]([N:5]1[C:9]2[CH:10]=[CH:11][C:12]([C:14]3[CH:15]=[N:16][C:17]([NH2:20])=[N:18][CH:19]=3)=[CH:13][C:8]=2[N:7]=[C:6]1[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][C:22]=1[C:31]1[O:30][C:29]([CH3:28])=[N:33][C:32]=1[CH3:34])([CH3:4])([CH3:3])[CH3:2]

参加物

8

反応物 4

HCID 10796Cesium carbonateHCID 11776TriphenylphosphineHCID 1389612,4-DimethyloxazoleHCID 585420695-[1-tert-butyl-2-(2-iodo-phenyl)-1H-benzimidazol-5-yl]-pyrimidin-2-ylamine

生成物 1

HCID 585419305-{1-tert-Butyl-2-[2-(2,4-dimethyl-oxazol-5-yl)-phenyl]-1H-benzimidazol-5-yl}-pyrimidin-2-ylamine収率 41%

試薬・触媒・溶媒 3

HCID 167845palladium(II) acetate触媒HCID 6228Dimethylformamide溶媒HCID 22728543Water ethylacetate溶媒

反応条件

温度
140 °C

実験手順

To a vial are added 5-[1-tert-butyl-2-(2-iodo-phenyl)-1H-benzimidazol-5-yl]-pyrimidin-2-ylamine (50 mg, 0.107 mmol), 2,4-dimethyl-oxazole (21 mg, 0.216 mol), palladium(II) acetate (5 mg, 0.022 mmol), PPh3 (6 mg, 0.023 mmol) and Cs2CO3 (70 mg, 0.215 mmol) in DMF (1.5 mL). The reaction mixture is stirred at 140° C. for 18 hours. The reaction mixture is diluted with EtOAc/water. The organic layer is separated, washed with brine, dried under anhydrous Na2SO4, filtered and concentrated. The residue is purified by silica gel flash column chromatography with 0-5% MeOH/CH2Cl2 as the eluent. The product fractions are collected and concentrated to afford the title compound (19 mg, 41%) as an off-white solid. LCMS (ESMS): m/z 439.86 (M++1)

後処理

  1. customThe organic layer is separated
  2. washwashed with brine
  3. customdried under anhydrous Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe residue is purified by silica gel flash column chromatography with 0-5% MeOH/CH2Cl2 as the eluent
  7. customThe product fractions are collected
  8. concentrationconcentrated

出典と根拠

ORDレコード
ord-c897844a27c649219e060d5138cf8e00
出典データセット
uspto-grants-2013_04
特許番号
US08420655B2

関連ノート

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