Tyramine → 4-[2-(4-Chloro-pyrimidin-2-ylamino)-ethyl]-phenol

HRID 2386433Notes

Reaction equation

HRID 2386433 reaction equation
Cl[C:2]1[N:7]=[C:6]([Cl:8])[CH:5]=[CH:4][N:3]=1.[NH2:9][CH2:10][CH2:11][C:12]1[CH:17]=[CH:16][C:15]([OH:18])=[CH:14][CH:13]=1>CN(C=O)C>[Cl:8][C:6]1[CH:5]=[CH:4][N:3]=[C:2]([NH:9][CH2:10][CH2:11][C:12]2[CH:17]=[CH:16][C:15]([OH:18])=[CH:14][CH:13]=2)[N:7]=1

Participants

4

Reactant 2

HCID 5610TyramineHCID 775312,4-Dichloropyrimidine

Product 1

HCID 866032814-[2-(4-Chloro-pyrimidin-2-ylamino)-ethyl]-phenolYield 15%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

2,4 dichloropyrimidine (1.49 g) was dissolved in DMF along with diisopropylethylmine (1.29 g) and tyramine (1.37 g.) The mixture was stirred at room temperature overnight. The mixture was partitioned between ethyl acetate and water and the organic layer washed with 1 N HCl followed by saturated NaHCO3 and brine. The solvent was removed and the residue subjected to flash chromatography (ethyl acetate as eluent.) 4-[2-(4-Chloro-pyrimidin-2-ylamino)-ethyl]-phenol eluted first and was isolate as a minor product (15% yield.) LC-MS showed the product had the expected M+H+ of 250.

Workup

  1. customThe mixture was partitioned between ethyl acetate and water
  2. washthe organic layer washed with 1 N HCl
  3. customThe solvent was removed
  4. customwas isolate as a minor product (15% yield.) LC-MS

Sources & evidence

ORD record
ord-7e5034d1c97a466eb72bddcfbdd7e379
Source dataset
uspto-grants-2012_09
Patent number
US08268822B2

Reaction notes

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