Hydrochloric Acid → HCID 18440618, compound

HRID 457694Notes

Reaction equation

HRID 457694 reaction equation
I[C:2]1[N:10]=[C:9]2[C:5]([N:6]=[CH:7][N:8]2[CH2:11][CH3:12])=[C:4]([NH2:13])[N:3]=1.[CH2:14]([SH:21])[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1.[OH-].[Na+].Cl>>[CH2:14]([S:21][C:2]1[N:10]=[C:9]2[C:5]([N:6]=[CH:7][N:8]2[CH2:11][CH3:12])=[C:4]([NH2:13])[N:3]=1)[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1

Participants

5

Reactant 4

HCID 313Hydrochloric AcidHCID 7509Benzyl mercaptanHCID 14798Sodium HydroxideHCID 184406199-Ethyl-2-iodo-9H-purin-6-amine

Product 1

HCID 18440618HCID 18440618, compound

Procedure

A mixture of 2-iodo-9-ethyl-9H-purin-6-ylamine (0.2 g, 0.69 mmol), 3 mL of benzyl mercaptan, and solid sodium hydroxide (200 mg, 5.0 mmol) was heated in a steel bomb at 100° C. for 24 hours. The reaction mixture was neutralized with 1N HCl and partitioned between water and chloroform. The organic layer was dried (Na2SO4), filtered and concentrated in vacuo, and the residue chromatographed on a silica gel column, eluting with a mixture of chloroform/methanol (97:3), to give 2-benzylthio-9-ethyl-9H-purin-6-ylamine, a compound of formula (4), as a chromatographically pure solid.

Workup

  1. custompartitioned between water and chloroform
  2. dry with materialThe organic layer was dried (Na2SO4)
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo
  5. customthe residue chromatographed on a silica gel column
  6. washeluting with a mixture of chloroform/methanol (97:3)

Sources & evidence

ORD record
ord-9a63cfd9e4b54c5482c69bf993e33a73
Source dataset
uspto-grants-2007_03
Patent number
US07189730B2

Reaction notes

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