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

HRID 2386411Notes

Reaction equation

HRID 2386411 reaction equation
[CH2:1]([O:5][C:6]1[CH:7]=[C:8]([C:12]2[CH:17]=[CH:16][N:15]=[C:14](Cl)[N:13]=2)[CH:9]=[CH:10][CH:11]=1)[CH2:2][CH2:3][CH3:4].[NH2:19][CH2:20][CH2:21][C:22]1[CH:27]=[CH:26][C:25]([OH:28])=[CH:24][CH:23]=1>>[CH2:1]([O:5][C:6]1[CH:7]=[C:8]([C:12]2[CH:17]=[CH:16][N:15]=[C:14]([NH:19][CH2:20][CH2:21][C:22]3[CH:27]=[CH:26][C:25]([OH:28])=[CH:24][CH:23]=3)[N:13]=2)[CH:9]=[CH:10][CH:11]=1)[CH2:2][CH2:3][CH3:4]

Participants

3

Reactant 2

HCID 5610TyramineHCID 866032734-(3-Butoxy-phenyl)-2-chloro-pyrimidine

Product 1

HCID 586035014-{2-[4-(3-Butoxy-phenyl)-pyrimidin-2-ylamino]-ethyl}-phenol

Procedure

Intermediate 46 was coupled with tyramine following procedure F. LC-MS showed the product had the expected M+H+ of 364. 1H NMR (Varian 300 MHz, CDCl3, shifts relative to the solvent peak at 7.24 ppm) δ 8.28 (m, 1H) 7.6 (m, 2H) 7.35 (m, 1H) 7.0 (m, 4H) 6.7 (d, 2H) 5.49 (br s, 1H) 4.0 (t, 2H) 3.7 (d, 2H) 2.85 (t, 2H) 1.78 (d, 2H) 1.5 (d, 2H) (t, 3H).

Sources & evidence

ORD record
ord-03a0e58e8dca4be9a3e6334362d23a4f
Source dataset
uspto-grants-2012_09
Patent number
US08268822B2

Reaction notes

Loading…