Potassium Hydroxide → 2,4-Diamino-6-ethyl-5-(3-(6-(3-ethoxycarbonylpropoxy)-2-methylquinolin-4-yloxy)propoxy)pyrimidine

HRID 40826Notes

Reaction equation

[NH2:1][C:2]1[N:7]=[C:6]([NH2:8])[C:5]([OH:9])=[C:4]([CH2:10][CH3:11])[N:3]=1.[OH-].[K+].[CH2:14]([O:16][C:17]([CH2:19][CH2:20][CH2:21][O:22][C:23]1[CH:24]=[C:25]2[C:30](=[CH:31][CH:32]=1)[N:29]=[C:28]([CH3:33])[CH:27]=[C:26]2[O:34][CH2:35][CH2:36][CH2:37]Br)=[O:18])[CH3:15]>CN(C=O)C>[NH2:1][C:2]1[N:7]=[C:6]([NH2:8])[C:5]([O:9][CH2:37][CH2:36][CH2:35][O:34][C:26]2[C:25]3[C:30](=[CH:31][CH:32]=[C:23]([O:22][CH2:21][CH2:20][CH2:19][C:17]([O:16][CH2:14][CH3:15])=[O:18])[CH:24]=3)[N:29]=[C:28]([CH3:33])[CH:27]=2)=[C:4]([CH2:10][CH3:11])[N:3]=1

Participants

Conditions

Temperature: 25 °C

Procedure

A mixture of 2,4-diamino-6-ethyl-5-hydroxypyrimidine (0.308 g, 2.0 mmol), potassium hydroxide (0.123 g, 2.2 mmol) and 3-(6-(3-ethoxycarbonylpropoxy)-2-methylquinolin-4-yloxy)propyl bromide (0.821 g, 2.0 mmol) in DMF was stirred at 25° C. overnight. The DMF was evaporated to dryness and the residue was purified by column chromatography over silica gel (4% MeOH: 96% CH2Cl2 as eluent). The product was obtained as a light yellow solid (0.3578 g, 37%). 1H NMR (400 MHz, DMSO-d6): 0.90 (3H, t, J=7.5 Hz), 1.16 (3H, t, J=7.1 Hz), 2.08 (2H, m), 2.28 (4H, m), 2.48 (2H, t, J=7.0 Hz), 2.56 (3H, s), 3.86 (2H, t, J=5.8 Hz), 4.06 (4H, m), 4.41 (2H, t, J=5.8 Hz), 5.53 (2H, s), 6.11 (2H, s) 6.93 (1H, s), 7.31 (1H, dd, J=9.1, 2.6 Hz), 7.37 (1H, d, J=2.6 Hz), 7.76 (1H, d, J=9.1 Hz).

Workup

customThe DMF was evaporated to dryness
customthe residue was purified by column chromatography over silica gel (4% MeOH: 96% CH2Cl2 as eluent)

Sources & evidence

ORD record: ord-48fca24a85254928aae90c6801bb6232
Source dataset: uspto-grants-2013_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08530491B2

Reaction notes

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