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

HRID 14815Notes

Reaction equation

HRID 14815 reaction equation
[CH2:1]([O:3][C:4]1[CH:9]=[CH:8][C:7]([C:10]2[CH:15]=[CH:14][N:13]=[C:12](Cl)[N:11]=2)=[CH:6][CH:5]=1)[CH3:2].[NH2:17][CH2:18][CH2:19][C:20]1[CH:25]=[CH:24][C:23]([OH:26])=[CH:22][CH:21]=1>>[CH2:1]([O:3][C:4]1[CH:9]=[CH:8][C:7]([C:10]2[CH:15]=[CH:14][N:13]=[C:12]([NH:17][CH2:18][CH2:19][C:20]3[CH:25]=[CH:24][C:23]([OH:26])=[CH:22][CH:21]=3)[N:11]=2)=[CH:6][CH:5]=1)[CH3:2]

Participants

3

Reactant 2

HCID 5610TyramineHCID 249019794-(4-Ethoxy-phenyl)-2-chloro-pyrimidine

Product 1

HCID 593410274-{2-[4-(4-Ethoxy-phenyl)-pyrimidin-2-ylamino]-ethyl}-phenol

Procedure

Intermediate 47 was coupled with tyramine following procedure F. LC-MS showed the product had the expected M+H+ of 336. 1H NMR (Varian 300 MHz, DMSO-d6, shifts relative to the solvent peak at 2.49 ppm) δ 8.2 (d, 1H), 8.0 (d, 2H) 7.0 (m, 4H) 6.6 (d, 3H), δ 4.0 (q, 2H), 3.4 (t, 2H), δ 2.7 (t, 2H), 1.3 (t, 3H).

Sources & evidence

ORD record
ord-b71b3ea1cb0e48f0bac7c9dfeba47a6e
Source dataset
uspto-grants-2010_06
Patent number
US07732444B2

Reaction notes

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