Sodium hydride → 5-Bromo-6-[2-(5-methylthiopyrimidin-2-yloxy)ethoxy]pyrimidine-4-amine

HRID 2315

Reaction equation

HRID 2315 reaction equation
[NH2:1][C:2]1[N:7]=[CH:6][N:5]=[C:4]([O:8][CH2:9][CH2:10][OH:11])[C:3]=1[Br:12].[H-].[Na+].Cl[C:16]1[N:21]=[CH:20][C:19]([S:22][CH3:23])=[CH:18][N:17]=1>CN(C)C=O>[Br:12][C:3]1[C:2]([NH2:1])=[N:7][CH:6]=[N:5][C:4]=1[O:8][CH2:9][CH2:10][O:11][C:16]1[N:21]=[CH:20][C:19]([S:22][CH3:23])=[CH:18][N:17]=1

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 189311062-(6-Amino-5-bromopyrimidin-4-yloxy)ethanolHCID 219795322-Chloro-5-(methylthio)pyrimidine

Product 1

HCID 196895255-Bromo-6-[2-(5-methylthiopyrimidin-2-yloxy)ethoxy]pyrimidine-4-amineYield 53.6%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 2-(6-amino-5-bromopyrimidin-4-yloxy)ethanol (611 mg) in dimethylformamide (20 ml) is added sodium hydride (60% dispersion-type, 125 mg), and the mixture is stirred for 20 minutes. To the mixture is added 2-chloro-5-methylthiopyrimidine (461 mg), and the mixture is stirred at room temperature for three hours. To the mixture is added ice-water, and the mixture is extracted with ethyl acetate. The ethyl acetate layer is washed, dried, and evaporated to remove the solvent. The residue is purified by silica get column chromatography (solvent; chloroform/methanol=20:1), and crystallized from ethyl acetate/diisopropyl ether to give 5-bromo-6-[2-(5-methythiopyrimidin-2-yloxy)ethoxy]pyrimidine-4-amine (501 mg).

Workup

  1. stirringthe mixture is stirred at room temperature for three hours
  2. extractionthe mixture is extracted with ethyl acetate
  3. washThe ethyl acetate layer is washed
  4. customdried
  5. customevaporated
  6. customto remove the solvent
  7. customThe residue is purified by silica
  8. customget column chromatography (solvent; chloroform/methanol=20:1)
  9. customcrystallized from ethyl acetate/diisopropyl ether

Sources & evidence

ORD record
ord-4bd91debc1224985b59b17dd05823067
Source dataset
uspto-grants-1998_03
Patent number
US05728706

Linked notes

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