Water → 2-Ethyl-4-pyrimidinamine

HRID 1411865Notes

Reaction equation

HRID 1411865 reaction equation
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]

Participants

7

Reactant 4

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

Product 1

HCID 139252962-Ethyl-4-pyrimidinamineYield 24.4%

Reagents, catalysts & solvents 2

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

Procedure

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

Workup

  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

Sources & evidence

ORD record
ord-749be335cb24400a82942eaeb9f68c70
Source dataset
uspto-grants-2014_12
Patent number
US08921353B2

Reaction notes

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