4-Aminophenethyl alcohol → 2-(4-((2-Cyclopentyl-6-ethylpyrimidin-4-yl)amino)phenyl)ethanol

HRID 1508931Notes

Reaction equation

HRID 1508931 reaction equation
Cl[C:2]1[CH:7]=[C:6]([CH2:8][CH3:9])[N:5]=[C:4]([CH:10]2[CH2:14][CH2:13][CH2:12][CH2:11]2)[N:3]=1.[NH2:15][C:16]1[CH:24]=[CH:23][C:19]([CH2:20][CH2:21][OH:22])=[CH:18][CH:17]=1>>[CH:10]1([C:4]2[N:3]=[C:2]([NH:15][C:16]3[CH:24]=[CH:23][C:19]([CH2:20][CH2:21][OH:22])=[CH:18][CH:17]=3)[CH:7]=[C:6]([CH2:8][CH3:9])[N:5]=2)[CH2:14][CH2:13][CH2:12][CH2:11]1

Participants

3

Reactant 2

HCID 669044-Aminophenethyl alcoholHCID 609214014-Chloro-2-cyclopentyl-6-ethylpyrimidine

Product 1

HCID 901098702-(4-((2-Cyclopentyl-6-ethylpyrimidin-4-yl)amino)phenyl)ethanolYield 92%

Procedure

Following General Procedure A2, 4-chloro-2-cyclopentyl-6-ethylpyrimidine (0.100 g, 0.47 mmol) was reacted with 4-aminophenethyl alcohol (0.078 g, 0.57 mmol) to afford the title compound (0.092 g, 92%) as an off-white solid. MW=311.42. 1H NMR (DMSO-d6, 500 MHz) δ 14.15 (s, 1H), 11.14 (s, 1H), 7.62 (s, 1H), 7.34-7.17 (m, 2H), 6.75 (s, 1H), 4.63 (s, 1H), 3.61 (t, J=6.9 Hz, 2H), 2.80-2.67 (m, 4H), 2.12-2.00 (m, 2H), 1.93-1.73 (m, 4H), 1.71-1.58 (m, 2H), 1.24 (s, 3H); APCI MS m/z 312 [M+H]+.

Sources & evidence

ORD record
ord-dce1840ec3fa4988af8e5d12a64c40ba
Source dataset
uspto-grants-2015_12
Patent number
US09221843B2

Reaction notes

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