2,4-Dichloropyridine → 5-((2-Chloropyridin-4-yl)oxy)pyrimidin-2-amine

HRID 2278925노트

반응식

HRID 2278925 반응식
[NH2:1][C:2]1[N:7]=[CH:6][C:5]([OH:8])=[CH:4][N:3]=1.CC(C)([O-])C.[K+].[Cl:15][C:16]1[CH:21]=[C:20](Cl)[CH:19]=[CH:18][N:17]=1>CC(N(C)C)=O.CCOC(C)=O>[Cl:15][C:16]1[CH:21]=[C:20]([O:8][C:5]2[CH:4]=[N:3][C:2]([NH2:1])=[N:7][CH:6]=2)[CH:19]=[CH:18][N:17]=1

참가 물질

6

반응물 3

HCID 335152,4-DichloropyridineHCID 177503882-Amino-5-hydroxypyrimidineHCID 23665647Potassium tert-butoxide

생성물 1

HCID 904034955-((2-Chloropyridin-4-yl)oxy)pyrimidin-2-amine수율 32.5%

시약·촉매·용매 2

HCID 8857Ethyl Acetate용매HCID 31374Dimethylacetamide용매2회

실험 절차

A solution of 2-amino-5-hydroxypyrimidine (1.00 g, 9.00 mmol) in DMA (25 mL) was treated with potassium tert-butoxide (1.24 g, 11.05 mmol). The thick mixture was stirred at room temperature for 1 h. To this was added a solution of 2,4-dichloropyridine (1.21 g, 8.18 mmol) in DMA (10 mL) and the reaction was stirred at RT overnight under Ar. The mixture was diluted with EtOAc (100 mL) and washed with water (100 mL). The organic phase was separated and the aqueous was extracted with EtOAc (100 mL). The combined EtOAc layers were washed with 5% LiCl (100 mL) and brine (100 mL) and then dried over sodium sulfate. The solvents were evaporated at reduced pressure to give 5-((2-chloropyridin-4-yl)oxy)pyrimidin-2-amine as a pale yellow solid (592 mg, 32%). MS (ESI) m/z: 223.0 (M+H+).

후처리

  1. stirringthe reaction was stirred at RT overnight under Ar
  2. washwashed with water (100 mL)
  3. customThe organic phase was separated
  4. extractionthe aqueous was extracted with EtOAc (100 mL)
  5. washThe combined EtOAc layers were washed with 5% LiCl (100 mL) and brine (100 mL)
  6. dry with materialdried over sodium sulfate
  7. customThe solvents were evaporated at reduced pressure

출처 및 근거

ORD 기록
ord-b16567d308ff474ebded485e25d77609
출처 데이터셋
uspto-grants-2015_09
특허 번호
US09133183B2

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