Lithium hydroxide, monohydrate → HCID 68953834, compound

HRID 40811Notes

Reaction equation

HRID 40811 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+].Br[CH2:16][CH2:17][CH2:18][N:19]1[C:27]2[C:22](=[CH:23][CH:24]=[CH:25][CH:26]=2)[CH:21]=[CH:20]1>CN(C=O)C.ClCCl>[NH2:1][C:2]1[N:7]=[C:6]([NH2:8])[C:5]([O:9][CH2:16][CH2:17][CH2:18][N:19]2[C:27]3[C:22](=[CH:23][CH:24]=[CH:25][CH:26]=3)[CH:21]=[CH:20]2)=[C:4]([CH2:10][CH3:11])[N:3]=1

Participants

6

Reactant 3

HCID 168937Lithium hydroxide, monohydrateHCID 118590271-(3-Bromopropyl)indoleHCID 205093882,4-Diamino-6-ethylpyrimidin-5-ol

Product 1

HCID 68953834HCID 68953834, compoundYield 48%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolvent2×HCID 6344DichloromethaneSolvent

Procedure

2,4-diamino-6-ethyl-5-hydroxypyrimidine (0.4625 g, 3 mmol) was added to a stirred solution of lithium hydroxide monohydrate (0.3147 g, 7.5 mmol) in DMF (2 mL) and the reaction mixture was stirred for 1 hour. A solution of 1-(3-bromopropyl)indole (0.7144 g, 3 mmol) in DMF (1 mL) was 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 and the residue was recrystallized from aqueous methanol. The product was obtained as a slightly yellow solid (0.4484 g, 48%). 1H NMR (DMSO-d6): 1.02 (3H, t, J=7.5 Hz), 2.20 (2H, m), 2.32 (2H, q, J=7.5 Hz), 3.60 (2H, t, J=6.3 Hz), 4.34 (2H, t, J=7.2 Hz), 5.56 (2H, s), 6.07 (2H, s), 6.43 (1H, d, J=3.1 Hz), 7.01 (1H, m), 7.13 (1H, m), 7.40 (1H, d, J=3.1 Hz), 7.50 (1H, d, J=8.3 Hz), 7.54 (1H, d, J=7.8 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. customthe residue was recrystallized from aqueous methanol

Sources & evidence

ORD record
ord-be023aa12eda4f3fb123681de37076e5
Source dataset
uspto-grants-2013_09
Patent number
US08530491B2

Reaction notes

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