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

HRID 1966752

반응식

HRID 1966752 반응식
[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]

참가 물질

8

반응물 4

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

생성물 1

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

시약·촉매·용매 3

HCID 167845palladium(II) acetate촉매HCID 6228Dimethylformamide용매HCID 22728543Water ethylacetate용매

반응 조건

온도
140 °C

실험 절차

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)

후처리

  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

출처 및 근거

ORD 기록
ord-c897844a27c649219e060d5138cf8e00
출처 데이터셋
uspto-grants-2013_04
특허 번호
US08420655B2

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