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

HRID 1049272ノート

反応式

HRID 1049272 の反応式
[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>[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

参加物

5

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 31374Dimethylacetamide溶媒2 回

実験手順

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 RT 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 partitioned into EtOAc (100 mL) and 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+).

後処理

  1. stirringthe reaction was stirred at RT overnight under Ar
  2. customThe mixture was partitioned into EtOAc (100 mL) and 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

出典と根拠

ORDレコード
ord-f828fcdf3d454aeb946d46615479bb2c
出典データセット
uspto-grants-2016_07
特許番号
US09382228B2

反応ノート

読み込み中…