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

HRID 1082311Notes

Reaction equation

HRID 1082311 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 gel 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 gel column chromatography (solvent; chloroform/methanol=20:1)
  8. customcrystallized from ethyl acetate/diisopropyl ether

Sources & evidence

ORD record
ord-e10b657869124f2994546fd93a3655f7
Source dataset
uspto-grants-1996_12
Patent number
US05589478

Reaction notes

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