Ammonia → HCID 178503829, compound

HRID 2269070Notes

Reaction equation

HRID 2269070 reaction equation
[NH2:1][C:2]1[N:10]=[C:9](Cl)[N:8]=[C:7]2[C:3]=1[N:4]=[C:5]([O:19]C)[N:6]2[CH2:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.[CH3:21][S:22][CH2:23][CH2:24][OH:25].[Na].Cl.N>>[NH2:1][C:2]1[N:10]=[C:9]([O:25][CH2:24][CH2:23][S:22][CH3:21])[N:8]=[C:7]2[C:3]=1[N:4]=[C:5]([OH:19])[N:6]2[CH2:12][C:13]1[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=1

Participants

6

Reactant 5

HCID 222AmmoniaHCID 313Hydrochloric AcidHCID 789252-(Methylthio)ethanolHCID 5360545SodiumHCID 18332697HCID 18332697, compound

Product 1

HCID 178503829HCID 178503829, compoundYield 27%

Procedure

6-amino-9-benzyl-2-chloro-8-methoxypurine (190 mg, 0.56 mmol) was added to 2-methylthioethanol (3 ml) containing sodium (110 mg, 4.78 mmol). The mixture was heated for 2 hours. Thereto were added 2N hydrochloric acid and 28% aqueous ammonia in order. The mixture was extracted with 3% methanol/chloroform and the organic layer was dried on sodium sulfate. After removal of the solvent in vacuo, the residue was purified by silica gel chromatography (3% methanol/chloroform) to give the subject compound (59 mg, yield 27%).

Workup

  1. temperatureThe mixture was heated for 2 hours
  2. extractionThe mixture was extracted with 3% methanol/chloroform
  3. customthe organic layer was dried on sodium sulfate
  4. customAfter removal of the solvent in vacuo
  5. customthe residue was purified by silica gel chromatography (3% methanol/chloroform)

Sources & evidence

ORD record
ord-dbffc342e289416d9cae361f59f8e757
Source dataset
uspto-grants-2001_12
Patent number
US06329381B1

Reaction notes

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