Triethylamine → HCID 4190857, compound

HRID 586418Notes

Reaction equation

HRID 586418 reaction equation
Cl[C:2]1[CH:7]=[C:6]([Cl:8])[N:5]=[C:4]([S:9][CH3:10])[N:3]=1.[CH:11]([N:14](CC)[CH:15](C)C)(C)C.C(N(CC)CC)C.Cl.CNC>O1CCCC1>[Cl:8][C:6]1[N:5]=[C:4]([S:9][CH3:10])[N:3]=[C:2]([N:14]([CH3:15])[CH3:11])[CH:7]=1

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 10473Dimethylamine, hydrochlorideHCID 805314,6-Dichloro-2-(methylthio)pyrimidineHCID 81531Diisopropylethylamine

Product 1

HCID 4190857HCID 4190857, compoundYield 73.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A mixture of 4,6-dichloro-2-(methylsulfanyl)pyrimidine (5.0 g, 26 mmol), N,N-diisopropylethylamine (3.1 g, 26 mmol), triethylamine (7.15 mL, 51 mmol), and N,N-dimethylamine hydrochloride (2.09 g, 26 mmol) in tetrahydrofuran (50 mL) was heated at reflux for 16 hours. The solvent was removed and the crude material was redissolved in EtOAc and washed with a solution of citric acid (2×100 mL), followed by water (2×100 mL) and brine (2×100 mL). The organic layers were combined, dried over anhydrous MgSO4, concentrated and purified by flash chromatography [eluent: EtOAc/hexane (1:19)], giving the desired product (3.89 g, 73%).

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 16 hours
  3. customThe solvent was removed
  4. dissolutionthe crude material was redissolved in EtOAc
  5. washwashed with a solution of citric acid (2×100 mL)
  6. dry with materialdried over anhydrous MgSO4
  7. concentrationconcentrated
  8. custompurified by flash chromatography [eluent: EtOAc/hexane (1:19)]

Sources & evidence

ORD record
ord-0e829a267f644ac68225c4ee649a8c1c
Source dataset
uspto-grants-2005_08
Patent number
US06936607B2

Reaction notes

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