Sodium Iodide → Ethyl 2-(2,3-dihydro-1H-indol-1-yl)-4-[(4-methoxybenzyl)oxy]-5-pyrimidinecarboxylate

HRID 7416

Reaction equation

HRID 7416 reaction equation
[OH:1][C:2]1[C:7]([C:8]([O:10][CH2:11][CH3:12])=[O:9])=[CH:6][N:5]=[C:4]([N:13]2[C:21]3[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=3)[CH2:15][CH2:14]2)[N:3]=1.C(=O)([O-])[O-].[K+].[K+].[I-].[Na+].[CH3:30][O:31][C:32]1[CH:39]=[CH:38][C:35]([CH2:36]Cl)=[CH:34][CH:33]=1>CN(C)C=O.O>[N:13]1([C:4]2[N:3]=[C:2]([O:1][CH2:36][C:35]3[CH:38]=[CH:39][C:32]([O:31][CH3:30])=[CH:33][CH:34]=3)[C:7]([C:8]([O:10][CH2:11][CH3:12])=[O:9])=[CH:6][N:5]=2)[C:21]2[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=2)[CH2:15][CH2:14]1

Participants

7

Reactant 4

HCID 5238Sodium IodideHCID 11430Potassium CarbonateHCID 699934-Methyloxybenzyl chlorideHCID 178418799HCID 178418799, compound

Product 1

HCID 21990432Ethyl 2-(2,3-dihydro-1H-indol-1-yl)-4-[(4-methoxybenzyl)oxy]-5-pyrimidinecarboxylateYield 78%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
80 °C

Procedure

To a solution of ethyl 4-hydroxy-2-(2,3-dihydro-1H-indol-1-yl)-5-pyrimidinecarboxylate (500 mg, 1.75 mmol) in N,N-dimethylformamide (10 mL) were added potassium carbonate (500 g, 4 mmol), sodium iodide (300 mg, 2 mmol) and 4-methoxybenzyl chloride (0.29 mL, 2 mmol), and the mixture was stirred at 80° C. for 18 h. The reaction mixture was allowed to cool to room temperature and water was added. The precipitated crystals were collected by filtration, washed several times with cold water and cold ether, and dried to give the title compound (550 mg, 78%).

Workup

  1. temperatureto cool to room temperature
  2. filtrationThe precipitated crystals were collected by filtration
  3. washwashed several times with cold water and cold ether
  4. customdried

Sources & evidence

ORD record
ord-4b9b0f31ba6b4ff9aace7ffd9d916a47
Source dataset
uspto-grants-2006_08
Patent number
US07087597B1

Linked notes

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