Hydrochloric Acid → HCID 178508405, compound

HRID 2269151Notes

Reaction equation

HRID 2269151 reaction equation
[H-].[Na+].[SH:3][CH2:4][CH2:5][C:6](O)=O.[NH2:9][C:10]1[N:18]=[C:17](Cl)[N:16]=[C:15]2[C:11]=1[N:12]=[CH:13][N:14]2[CH2:20][C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1.Cl.[Cl-].[Na+].[OH2:30]>CN(C=O)C>[NH2:9][C:10]1[N:18]=[C:17]([CH2:6][CH2:5][C:4]([OH:30])=[S:3])[N:16]=[C:15]2[C:11]=1[N:12]=[CH:13][N:14]2[CH2:20][C:21]1[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=1

Participants

7

Reactant 5

HCID 313Hydrochloric AcidHCID 65143-Mercaptopropionic AcidHCID 24758Sodium hydrideHCID 2764829-Benzyl-2-chloro-9h-purin-6-amineHCID 57417360Sodium chloride; water

Product 1

HCID 178508405HCID 178508405, compoundYield 47%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
100 °C

Procedure

To sodium hydride (300 mg, 7.5 mmol 60% in mineral oil) were added DMF (10 ml), 3-mercaptopropionic acid (1 ml, 11 mmol) and 6-amino-9-benzyl-2-chloropurine (200 mg, 0.77 mmol) in order. The mixture was stirred at 100° C. for 5 hours. After addition of saturated brine, the reaction mixture was acidified with 2N hydrochloric acid and extracted with chloroform. The organic layer was dried on magnesium sulfate and concentrated in vacuo to dryness. The residue was purified with silica gel chromatography (4% methanol/chloroform) to give the subject compound (120 mg, yield 47%).

Workup

  1. extractionextracted with chloroform
  2. customThe organic layer was dried on magnesium sulfate
  3. concentrationconcentrated in vacuo to dryness
  4. customThe residue was purified with silica gel chromatography (4% methanol/chloroform)

Sources & evidence

ORD record
ord-a7c50d6abda34628b9c7054135998ff4
Source dataset
uspto-grants-2001_12
Patent number
US06329381B1

Reaction notes

Loading…