Triethylamine → HCID 21473649, compound

HRID 2294017Notes

Reaction equation

HRID 2294017 reaction equation
Cl[CH2:2][C:3]1[C:4]([NH2:10])=[N:5][C:6]([CH3:9])=[N:7][CH:8]=1.C(N(CC)CC)C.[CH2:18]([C:20]1[CH2:21][CH2:22][NH:23][CH2:24][CH:25]=1)[CH3:19]>CN(C)C=O>[CH2:18]([C:20]1[CH2:25][CH2:24][N:23]([CH2:2][C:3]2[C:4]([NH2:10])=[N:5][C:6]([CH3:9])=[N:7][CH:8]=2)[CH2:22][CH:21]=1)[CH3:19]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 4212454-Amino-5-(chloromethyl)-2-methylpyrimidineHCID 21473622HCID 21473622, compound

Product 1

HCID 21473649HCID 21473649, compoundYield 52%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A suspension of 0.95 g (0.0050 mol) of 5-chloromethyl-2-methyl-pyrimidin-4-ylamine in 13 ml of dimethylformamide was treated with 3.5 ml (0.025 mol) of triethylamine and 1.16 g (0.010) of 4-ethyl-1,2,3,6-tetrahydropyridine and the mixture was stirred at room temperature under argon for 18 hours. The solvent was distilled off in a high vacuum. The residue was partitioned between dichloromethane/water, extracted and dried over MgSO4. After removing the solvent the residue was chromatographed on silica gel with ethyl acetate as the eluent. 0.60 g (52%) of 5-(4-ethyl-3,6-dihydro-2H-pyridin-1-ylmethyl)-2-methyl-pyrimidin-4-ylamine were obtained as a beige solid; m.p. 75°-76°.

Workup

  1. distillationThe solvent was distilled off in a high vacuum
  2. customThe residue was partitioned between dichloromethane/water
  3. extractionextracted
  4. dry with materialdried over MgSO4
  5. customAfter removing the solvent the residue
  6. customwas chromatographed on silica gel with ethyl acetate as the eluent

Sources & evidence

ORD record
ord-e1c4fa5adb774828a108934667006266
Source dataset
uspto-grants-1997_11
Patent number
US05688798

Reaction notes

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