Triethylamine → HCID 70193092, compound

HRID 2294018Notes

Reaction equation

HRID 2294018 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.[C:18]([O:26][CH2:27][CH:28]1[CH:33]=[CH:32][NH:31][CH2:30][CH2:29]1)(=[O:25])[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1>CN(C)C=O>[C:18]([O:26][CH2:27][C:28]1[CH2:33][CH2:32][N:31]([CH2:2][C:3]2[C:4]([NH2:10])=[N:5][C:6]([CH3:9])=[N:7][CH:8]=2)[CH2:30][CH:29]=1)(=[O:25])[C:19]1[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 4212454-Amino-5-(chloromethyl)-2-methylpyrimidineHCID 70195297HCID 70195297, compound

Product 1

HCID 70193092HCID 70193092, compoundYield 74%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A suspension of 0.195 g (0.0010 mol) of 5-chloromethyl-2-methyl-pyrimidin-4-ylamine in 5 ml of dimethylformamide was treated with 0.42 ml (0.0030 mol) of triethylamine and 0.365 g (0.0010 mol) of 1,2,3,4-tetrahydro-pyridin-4-ylmethyl benzoate 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 over silica gel with ethyl acetate as the eluent. 0.17 g (74%) of 1-(4-amino-2-methyl-pyrimidin-5-ylmethyl)-1,2,3,6-tetrahydro-pyridin-4-ylmethyl benzoate was obtained as a yellow oil. MS (ISP): me/e=339 (C19 H23N4O2+).

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 over silica gel with ethyl acetate as the eluent

Sources & evidence

ORD record
ord-d1fb8fa124be40329c2eff9d8e21b059
Source dataset
uspto-grants-1997_11
Patent number
US05688798

Reaction notes

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