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

HRID 2386415Notes

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])=[C:22]([O:27][CH3:28])[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])=[C:22]([O:27][CH3:28])[CH:21]=3)[N:11]=2)=[CH:6][CH:5]=1)[CH3:2]

Participants

Reactant 2

HCID 16693-Methoxytyramine

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

Product 1

HCID 586035604-{2-[4-(4-Ethoxy-phenyl)-pyrimidin-2-ylamino]-ethyl}-2-methoxy-phenol

Procedure

Intermediate 47 was coupled with 4-(2-Amino-ethyl)-2-methoxy-phenol following procedure F. LC-MS showed the product had the expected M+H+ of 366. 1H NMR (Varian 300 MHz, DMSO-d6, shifts relative to the solvent peak at 2.49 ppm) δ 8.0 (d, 1H), 7.1-7.0 (m, 4H) 6.8 (s, 1H), δ 6.7-6.6 (m, 3H), δ 4.0 (q, 2H), δ 3.7 (s, 3H), 3.5 (t, 2H), δ 2.7 (t, 2H), 1.3 (t, 3H).

Sources & evidence

ORD record: ord-4a84dc489c8c4b6da973f1ff733a51aa
Source dataset: uspto-grants-2012_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08268822B2

Reaction notes

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