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

HRID 2386408Notes

Reaction equation

HRID 2386408 reaction equation
Cl[C:2]1[N:7]=[C:6]([C:8]2[CH:13]=[CH:12][CH:11]=[C:10]([O:14][CH:15]([CH3:17])[CH3:16])[CH:9]=2)[CH:5]=[CH:4][N:3]=1.[NH2:18][CH2:19][CH2:20][C:21]1[CH:26]=[CH:25][C:24]([OH:27])=[CH:23][CH:22]=1>>[CH:15]([O:14][C:10]1[CH:9]=[C:8]([C:6]2[CH:5]=[CH:4][N:3]=[C:2]([NH:18][CH2:19][CH2:20][C:21]3[CH:26]=[CH:25][C:24]([OH:27])=[CH:23][CH:22]=3)[N:7]=2)[CH:13]=[CH:12][CH:11]=1)([CH3:17])[CH3:16]

Participants

3

Reactant 2

HCID 5610TyramineHCID 249018192-Chloro-4-(3-isopropoxy-phenyl)-pyrimidine

Product 1

HCID 586034004-{2-[4-(3-Isopropoxy-phenyl)-pyrimidin-2-ylamino]-ethyl}-phenol

Procedure

Intermediate 45 was coupled with tyramine following procedure F. LC-MS showed the product had the expected M+H+ of 350. 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) 6.68 (m, 2H) 5.5 (m, 1H) 4.62 (m, 1H) 3.71 (m, 2H) 2.85 (m, 2H) 1.32 (d, 6H).

Sources & evidence

ORD record
ord-37214b22cc124d4da949a3abb4aa6284
Source dataset
uspto-grants-2012_09
Patent number
US08268822B2

Reaction notes

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