Triethylamine → HCID 90425669, compound

HRID 527459Notes

Reaction equation

HRID 527459 reaction equation
[Cl:1][C:2]1[N:7]=[C:6]([Cl:8])[CH:5]=[C:4](Cl)[N:3]=1.C(N(CC)CC)C.[CH3:17][NH:18][CH:19]1[CH2:24][CH2:23][O:22][CH2:21][CH2:20]1>CCO>[Cl:1][C:2]1[N:3]=[C:4]([N:18]([CH3:17])[CH:19]2[CH2:24][CH2:23][O:22][CH2:21][CH2:20]2)[CH:5]=[C:6]([Cl:8])[N:7]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 773782,4,6-TrichloropyrimidineHCID 69919504-(Methylamino)tetrahydro-2H-pyran

Product 1

HCID 90425669HCID 90425669, compoundYield 66.1%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of 2,4,6-trichloro-pyrimidine (9.2 g, 50 mmol) and triethylamine (10.1 g, 100 mmol) in EtOH (100 mL) was added N-methyltetrahydro-2H-pyran-4-amine (5.17 g, 45 mmol) dropwise at −40° C. The mixture was warmed up to room temperature then stirred for 14 h., quenched with H2O (25 mL), concentrated and the residue was extracted with EtOAc (100 mL×3). The combined organic layers were dried over Na2SO4, filtered and concentrated. The residue was purified by chromatographic column on silica gel (petroleum ether/EtOAc=30/1 to 2/1) to give (2,6-dichloro-pyrimidin-4-yl)-methyl-(tetrahydro-pyran-4-yl)amine as white solid (7.8 g, 60% yield). ESI-LCMS (m/z): 263.14 [M+1]+;

Workup

  1. customquenched with H2O (25 mL)
  2. concentrationconcentrated
  3. extractionthe residue was extracted with EtOAc (100 mL×3)
  4. dry with materialThe combined organic layers were dried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe residue was purified by chromatographic column on silica gel (petroleum ether/EtOAc=30/1 to 2/1)

Sources & evidence

ORD record
ord-291e8c7ec3794c67b6bd684e6c5894b9
Source dataset
uspto-grants-2016_05
Patent number
US09346802B2

Reaction notes

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