Potassium Carbonate → tert-Butyl [5-(2-{3-[(2,5-dichloropyrimidin-4-yl)amino]phenyl}ethyl)pyridin-3-yl]carbamate

HRID 541868노트

반응식

HRID 541868 반응식
[NH2:1][C:2]1[CH:3]=[C:4]([CH2:8][CH2:9][C:10]2[CH:11]=[C:12]([NH:16][C:17](=[O:23])[O:18][C:19]([CH3:22])([CH3:21])[CH3:20])[CH:13]=[N:14][CH:15]=2)[CH:5]=[CH:6][CH:7]=1.[Cl:24][C:25]1[N:30]=[C:29](Cl)[C:28]([Cl:32])=[CH:27][N:26]=1.C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O>[Cl:24][C:25]1[N:30]=[C:29]([NH:1][C:2]2[CH:3]=[C:4]([CH2:8][CH2:9][C:10]3[CH:11]=[C:12]([NH:16][C:17](=[O:23])[O:18][C:19]([CH3:20])([CH3:22])[CH3:21])[CH:13]=[N:14][CH:15]=3)[CH:5]=[CH:6][CH:7]=2)[C:28]([Cl:32])=[CH:27][N:26]=1

참가 물질

5

반응물 3

HCID 11430Potassium CarbonateHCID 2372592,4,5-TrichloropyrimidineHCID 57961822tert-Butyl {5-[2-(3-aminophenyl)ethyl]pyridin-3-yl}carbamate

생성물 1

HCID 57962432tert-Butyl [5-(2-{3-[(2,5-dichloropyrimidin-4-yl)amino]phenyl}ethyl)pyridin-3-yl]carbamate수율 82%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

To a solution of tert-butyl {5-[2-(3-aminophenyl)ethyl]pyridin-3-yl}carbamate (0.50 g, 1.6 mmol) and 2,4,5-trichloropyrimidine (0.30 g, 1.6 mmol) in N,N-dimethylformamide (4 mL) was added potassium carbonate (0.43 g, 3.11 mmol). The resultant mixture was stirred overnight at room temperature. The reaction was quenched with water. EtOAc was added and the layers were separated. The aqueous layer was extracted with EtOAc once. The combined organic layers were washed with water and brine then dried (Na2SO4), filtered, and concentrated. The crude mixture was purified by silica gel column chromatography to give the desired product as a white powder (0.60 g, 82%). LCMS for C22H24Cl2N5O2 (M+H)+: m/z=460.1, 462.1.

후처리

  1. customThe reaction was quenched with water
  2. additionEtOAc was added
  3. customthe layers were separated
  4. extractionThe aqueous layer was extracted with EtOAc once
  5. washThe combined organic layers were washed with water and brine
  6. dry with materialthen dried (Na2SO4)
  7. filtrationfiltered
  8. concentrationconcentrated
  9. customThe crude mixture was purified by silica gel column chromatography

출처 및 근거

ORD 기록
ord-59f57c990cd64649a0ca957a1fc7713c
출처 데이터셋
uspto-grants-2014_10
특허 번호
US08871753B2

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