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

HRID 40799Notes

Reaction equation

HRID 40799 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+].S(O[CH2:20][CH2:21][CH2:22][O:23][C:24]1[C:33]2[C:28](=[CH:29][CH:30]=[CH:31][CH:32]=2)[N:27]=[CH:26][CH:25]=1)(=O)(=O)C>CN(C=O)C.ClCCl>[NH2:1][C:2]1[N:7]=[C:6]([NH2:8])[C:5]([O:9][CH2:20][CH2:21][CH2:22][O:23][C:24]2[C:33]3[C:28](=[CH:29][CH:30]=[CH:31][CH:32]=3)[N:27]=[CH:26][CH:25]=2)=[C:4]([CH2:10][CH3:11])[N:3]=1

Participants

6

Reactant 3

HCID 168937Lithium hydroxide, monohydrateHCID 205093882,4-Diamino-6-ethylpyrimidin-5-olHCID 866295403-(Quinolin-4-yloxy)propyl mesylate

Product 1

HCID 252629242,4-Diamino-6-ethyl-5-(3-(quinolin-4-yloxy)propoxy)pyrimidineYield 100.6%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolvent2×HCID 6344DichloromethaneSolvent

Procedure

2,4-diamino-6-ethyl-5-hydroxypyrimidine (0.3963 g, 2.6 mmol) was added to a stirred solution of lithium hydroxide monohydrate (497.2 mg, 11.8 mmol) in DMF (2 mL) and the reaction mixture was stirred for 1 hour. A solution of 3-(quinolin-4-yloxy)-propyl mesylate (0.3868 g, 1.37 mmol) in DMF (1 mL) was slowly added and the reaction mixture was left stirring at 25° C. overnight. The reaction was diluted with dichloromethane and extracted with water. The dichloromethane layer was evaporated followed by crystallization of the residue from aqueous methanol. The product was obtained as a slightly yellow solid (0.4677 g, 53%). 1H NMR (400 MHz, DMSO-d6): 0.87 (3H, t, J=7.0 Hz), 2.24 (2H, q, J=7.0 Hz), 2.30 (2H, m), 3.85 (2H, t, J=5.5 Hz), 4.43 (2H, t, J=5.5 Hz), 5.53 (2H, s), 6.11 (2H, s), 7.06 (1H, d, J=5.2 Hz), 7.54 (1H, t, J=8.0 Hz), 7.72 (1H, ddd, J=1.4, 6.9, 8.3 Hz), 7.93 (1H, d, J=8.3 Hz), 8.15 (1H, d, J=8.5 Hz), 8.72 (1H, d, J=5.2 Hz).

Workup

  1. waitthe reaction mixture was left
  2. stirringstirring at 25° C. overnight
  3. extractionextracted with water
  4. customThe dichloromethane layer was evaporated
  5. customfollowed by crystallization of the residue from aqueous methanol

Sources & evidence

ORD record
ord-131b69883db14b22a69f4f0dd8800644
Source dataset
uspto-grants-2013_09
Patent number
US08530491B2

Reaction notes

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