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

HRID 14844

Reaction equation

HRID 14844 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][CH2:9][NH:10][C:11]2[N:16]=[C:15]([C:17]3[CH:18]=[C:19]([CH:22]=[CH:23][CH:24]=3)[CH:20]=O)[CH:14]=[CH:13][N:12]=2)=[CH:4][CH:3]=1.[CH2:25]([NH2:27])[CH3:26]>>[CH2:25]([NH:27][CH2:20][C:19]1[CH:18]=[C:17]([C:15]2[CH:14]=[CH:13][N:12]=[C:11]([NH:10][CH2:9][CH2:8][C:5]3[CH:6]=[CH:7][C:2]([OH:1])=[CH:3][CH:4]=3)[N:16]=2)[CH:24]=[CH:23][CH:22]=1)[CH3:26]

Participants

3

Reactant 2

HCID 6341EthylamineHCID 866032623-{2-[2-(4-Hydroxy-phenyl)-ethylamino]-pyrimidin-4-yl}-benzaldehyde

Product 1

HCID 586034844-{2-[4-(3-Ethylaminomethyl-phenyl)-pyrimidin-2-ylamino]-ethyl}-phenol

Procedure

Intermediate 28 was coupled with ethylamine following procedure B. LC-MS showed the product had the expected M+H+ of 349. 1H NMR (Varian 300 MHz, CDCl3, shifts relative to the solvent peak at 7.24 ppm) δ 8.3 (d, 1H) 7.9 (m, 2H) 7.4 (m, 2H) 7.0 (d, 2H) 6.9 (d, 1H) 6.7 (d, 2H) 5.2 (m, 1H) 3.9 (s, 2H) 3.7 (m, 2H) 2.8 (m, 2H) 2.7 (m, 2H) 1.2 (m, 3H).

Sources & evidence

ORD record
ord-1e3d1908e8ee45018cf992f3d6647c41
Source dataset
uspto-grants-2010_06
Patent number
US07732444B2

Linked notes

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