Lithium hydroxide, monohydrate → 2,4-Diamino-6-ethyl-5-(3-(2-methylquinolin-4-yloxy)propoxy)pyrimidine

HRID 40806Notes

Reaction equation

HRID 40806 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.O.[OH-].[Li+].[CH3:15][C:16]1[CH:25]=[C:24]([O:26][CH2:27][CH2:28][CH2:29]Br)[C:23]2[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=2)[N:17]=1>CN(C=O)C>[NH2:1][C:2]1[N:7]=[C:6]([NH2:8])[C:5]([O:9][CH2:29][CH2:28][CH2:27][O:26][C:24]2[C:23]3[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=3)[N:17]=[C:16]([CH3:15])[CH:25]=2)=[C:4]([CH2:10][CH3:11])[N:3]=1

Participants

5

Reactant 3

HCID 168937Lithium hydroxide, monohydrateHCID 205093882,4-Diamino-6-ethylpyrimidin-5-olHCID 685750213-(2-Methylquinolin-4-yloxy)propyl bromide

Product 1

HCID 252629222,4-Diamino-6-ethyl-5-(3-(2-methylquinolin-4-yloxy)propoxy)pyrimidineYield 47%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
25 °C

Procedure

A mixture of 2,4-diamino-6-ethyl-5-hydroxypyrimidine (0.539 g, 3.5 mmol) and lithium hydroxide monohydrate (0.294 g, 7.0 mmol) in DMF (10 mL) was stirred at 25° C. for 1 hour after that 3-(2-methylquinolin-4-yloxy)propyl bromide (0.980 g, 3.5 mmol) was added to the reaction mixture and the reaction mixture was left to stir at 25° C. overnight. Two thirds of the DMF was evaporated under vacuum and the reaction mixture was poured in water, solid was separated by filtration and dried in oven at 80° C. The crude product was purified by column chromatography on silica gel (4% MeOH: 96% CH2Cl2 as eluent) to obtain title compound as light yellow solid (0.5814 g, 47%). 1H NMR (400 MHz, DMSO-d6): 0.90 (3H, t, J=7.6 Hz), 2.30 (4H, m), 2.60 (3H, s), 3.86 (2H, t, J=5.9 Hz), 4.41 (2H, t, J=5.9 Hz), 5.59 (2H, s), 6.16 (2H, s), 6.97 (1H, s), 7.46 (1H, t, J=7.7 Hz), 7.67 (1H, t, J=7.7 Hz), 7.84 (1H, d, J=8.4 Hz), 8.09 (1H, d, J=8.2 Hz).

Workup

  1. additionwas added to the reaction mixture
  2. waitthe reaction mixture was left
  3. customTwo thirds of the DMF was evaporated under vacuum
  4. additionthe reaction mixture was poured in water
  5. customsolid was separated by filtration
  6. customdried in oven at 80° C
  7. customThe crude product was purified by column chromatography on silica gel (4% MeOH: 96% CH2Cl2 as eluent)

Sources & evidence

ORD record
ord-494b16a359284e45a63df0e673c026fc
Source dataset
uspto-grants-2013_09
Patent number
US08530491B2

Reaction notes

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