Acetonitrile → 4-(2-(4-Nitrophenoxy)phenyl)pyrimidin-2-amine

HRID 227807

반응식

HRID 227807 반응식
CC1(C)C(C)(C)OB([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=2[O:15][C:16]2[CH:21]=[CH:20][C:19]([N+:22]([O-:24])=[O:23])=[CH:18][CH:17]=2)O1.C([O-])(=O)C.[K+].Cl[C:32]1[CH:37]=[CH:36][N:35]=[C:34]([NH2:38])[N:33]=1.C(#N)C>C(Cl)Cl.O>[N+:22]([C:19]1[CH:18]=[CH:17][C:16]([O:15][C:10]2[CH:11]=[CH:12][CH:13]=[CH:14][C:9]=2[C:32]2[CH:37]=[CH:36][N:35]=[C:34]([NH2:38])[N:33]=2)=[CH:21][CH:20]=1)([O-:24])=[O:23]

참가 물질

7

반응물 4

HCID 6342AcetonitrileHCID 2233322-Amino-4-chloropyrimidineHCID 517044Potassium AcetateHCID 667316814,4,5,5-Tetramethyl-2-(2-(4-nitrophenoxy)phenyl)-1,3,2-dioxaborolane2회

생성물 1

HCID 667316394-(2-(4-Nitrophenoxy)phenyl)pyrimidin-2-amine

시약·촉매·용매 2

HCID 962Water용매2회HCID 6344Dichloromethane용매

반응 조건

온도
85 °C

실험 절차

The compound of step 1 (0.034 g, 0.054 mmol), potassium acetate (0.26 g, 2.7 mmol), 4,4,5,5-tetramethyl-2-(2-(4-nitrophenoxy)phenyl)-1,3,2-dioxaborolane (0.460 g, 1.3 mmol), and 4-chloropyrimidin-2-amine (0.17 g, 1.3 mmol) were combined in a sealed tube under nitrogen, to which 7 nL ACN and water (0.73 ml, 40 mmol) were added. The reaction was sealed and heated to 85° C. overnight. The reaction was diluted with DCM and water, and extracted 2× with DCM. The combined organics were dried over anhydrous sodium sulfate, filtered, and concentrated in vacuo. The resulting material was purified by silica gel chromatography (MeOH/DCM) to give 4-(2-(4-nitrophenoxy)phenyl)pyrimidin-2-amine as a white solid MS m/z=309 [M+H]+. Calc'd for C16H12N4O3: 308.3.

후처리

  1. additionwere added
  2. customThe reaction was sealed
  3. extractionextracted 2× with DCM
  4. dry with materialThe combined organics were dried over anhydrous sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customThe resulting material was purified by silica gel chromatography (MeOH/DCM)

출처 및 근거

ORD 기록
ord-925a179aa6d24f6197f6dc0071004c16
출처 데이터셋
uspto-grants-2009_07
특허 번호
US07560551B2

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