Tyramine → 4-{2-[4-(3-Dimethoxymethyl-phenyl)-pyrimidin-2-ylamino]-ethyl}-phenol

HRID 14784

Reaction equation

HRID 14784 reaction equation
Cl[C:2]1[N:7]=[C:6]([C:8]2[CH:13]=[CH:12][CH:11]=[C:10]([CH:14]([O:17][CH3:18])[O:15][CH3:16])[CH:9]=2)[CH:5]=[CH:4][N:3]=1.[NH2:19][CH2:20][CH2:21][C:22]1[CH:27]=[CH:26][C:25]([OH:28])=[CH:24][CH:23]=1>>[CH3:16][O:15][CH:14]([O:17][CH3:18])[C:10]1[CH:9]=[C:8]([C:6]2[CH:5]=[CH:4][N:3]=[C:2]([NH:19][CH2:20][CH2:21][C:22]3[CH:27]=[CH:26][C:25]([OH:28])=[CH:24][CH:23]=3)[N:7]=2)[CH:13]=[CH:12][CH:11]=1

Participants

3

Reactant 2

HCID 5610TyramineHCID 866032612-Chloro-4-(3-dimethoxymethyl-phenyl)-pyrimidine

Product 1

HCID 670450574-{2-[4-(3-Dimethoxymethyl-phenyl)-pyrimidin-2-ylamino]-ethyl}-phenolYield 35%

Procedure

Intermediate 26 was coupled with tyramine following procedure F. The product was purified by flash chromatography using 99:1 CH2Cl2:MeOH as eluent. Yield: 35%. LC-MS showed the product had the expected M+H+ of 366.

Workup

  1. customThe product was purified by flash chromatography

Sources & evidence

ORD record
ord-571c36ad8b334d5587622f912b5c2a15
Source dataset
uspto-grants-2010_06
Patent number
US07732444B2

Linked notes

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