2-Mercaptoethanol → HCID 178508214, compound

HRID 1636295Notes

Reaction equation

HRID 1636295 reaction equation
[NH2:1][C:2]1[N:10]=[C:9]2[C:5]([N:6]=[CH:7][N:8]2[CH:11]2[CH2:16][S:15][CH:14](CO)[CH2:13][O:12]2)=[C:4](Cl)[N:3]=1.SC[CH2:22][OH:23].C[O-:25].[Na+]>CO>[OH:23][CH2:22][SH:15]1[CH2:14][CH2:13][O:12][CH:11]([N:8]2[CH:7]=[N:6][C:5]3[C:4](=[O:25])[NH:3][C:2]([NH2:1])=[N:10][C:9]2=3)[CH2:16]1

Participants

5

Reactant 3

HCID 15672-MercaptoethanolHCID 10942334Sodium MethoxideHCID 19350818HCID 19350818, compound

Product 1

HCID 178508214HCID 178508214, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

2-Amino-6-chloro-9-(5-hydroxymethyl-1,4-oxathian-2-yl)purine (0.03 g) was dissolved in methanol (10 ml), and 2-mercaptoethanol (0.03 ml) and 1M, sodium methoxide solution (0.01 ml) were added thereto. The resultant mixture was stirred under reflux for three days. After concentrating the reaction mixture under reduced pressure, water was added thereto, and the aqueous layer was washed several times with ethyl ether. Acetic acid was added thereto to adjust pH of the aqueous layer to 7, and the solvent was distilled off under reduced pressure. The residue was purified on a silica gel column (eluent: chloroform/methanol=5/1) to obtain the desired product (0.02 g) as pale yellow solid.

Workup

  1. temperatureunder reflux for three days
  2. concentrationAfter concentrating the reaction mixture under reduced pressure, water
  3. additionwas added
  4. washthe aqueous layer was washed several times with ethyl ether
  5. additionAcetic acid was added
  6. distillationthe solvent was distilled off under reduced pressure
  7. customThe residue was purified on a silica gel column (eluent: chloroform/methanol=5/1)

Sources & evidence

ORD record
ord-d31974c5d16343f99d409ea68e28f20b
Source dataset
uspto-grants-2000_03
Patent number
US06034087

Reaction notes

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