Water → 2-Ethyl-4-pyrimidinamine

HRID 592926

反応式

HRID 592926 の反応式
Cl[C:2]1[N:7]=[C:6]([NH2:8])[CH:5]=[CH:4][N:3]=1.[CH2:9](B(CC)CC)[CH3:10].[O-]P([O-])([O-])=O.[K+].[K+].[K+].O>C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.Cl[Pd]Cl.[Fe+2].O1CCCC1>[CH2:9]([C:2]1[N:7]=[C:6]([NH2:8])[CH:5]=[CH:4][N:3]=1)[CH3:10]

参加物

7

反応物 4

HCID 962WaterHCID 7357TriethylboraneHCID 62657Potassium Phosphate, TribasicHCID 3457522-Chloro-4-aminopyrimidine

生成物 1

HCID 139252962-Ethyl-4-pyrimidinamine収率 24.4%

試薬・触媒・溶媒 2

HCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)触媒HCID 8028Tetrahydrofuran溶媒

実験手順

A 100-mL single-neck round-bottomed flask equipped with a magnetic stirrer and a reflux condenser was charged with 2-chloropyrimidin-4-amine (2.60 g, 20.0 mmol), triethylborane (20.0 mL, 1.0 M in THF, 20.0 mmol), Pd(dppf)Cl2 (816 mg, 1.0 mmol), K3PO4 (13.0 g, 40.0 mmol), water (2 mL), and tetrahydrofuran (50 mL). After three cycles of vacuum/argon flush, the mixture was heated at reflux for 14 h. It was then cooled to room temperature and filtered. The filtrate was concentrated under reduced pressure and the resulting residue was purified by silica-gel column chromatography eluting with 40:1 dichloromethane/methanol to afford 229a as yellow solid (600 mg, 24%). MS-ESI: [M+H]+ 124.3

後処理

  1. customA 100-mL single-neck round-bottomed flask equipped with a magnetic stirrer and a reflux condenser
  2. customAfter three cycles of vacuum/argon flush
  3. temperaturethe mixture was heated
  4. temperatureat reflux for 14 h
  5. filtrationfiltered
  6. concentrationThe filtrate was concentrated under reduced pressure
  7. customthe resulting residue was purified by silica-gel column chromatography
  8. washeluting with 40:1 dichloromethane/methanol

出典と根拠

ORDレコード
ord-bc12d6b4019e45538053503a395015a9
出典データセット
uspto-grants-2016_01
特許番号
US09238655B2

関連ノート

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