Ammonia → HCID 178509025, compound

HRID 2269017Notes

Reaction equation

HRID 2269017 reaction equation
[NH2:1][C:2]1[N:10]=[C:9]([S:11][C:12]2[CH:21]=[CH:20][C:19]3[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=3)[CH:13]=2)[N:8]=[C:7]2[C:3]=1[N:4]=[C:5](Br)[N:6]2[CH2:22][C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1.Cl.N.CS(C)=[O:34]>>[NH2:1][C:2]1[N:10]=[C:9]([S:11][C:12]2[CH:21]=[CH:20][C:19]3[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=3)[CH:13]=2)[N:8]=[C:7]2[C:3]=1[N:4]=[C:5]([OH:34])[N:6]2[CH2:22][C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1

Participants

5

Reactant 4

HCID 222AmmoniaHCID 313Hydrochloric AcidHCID 679Dimethyl SulfoxideHCID 15546319HCID 15546319, compound

Product 1

HCID 178509025HCID 178509025, compoundYield 35%

Procedure

6-Amino-9-benzyl-8-bromo-2-(2-naphthylthio)purine (33 mg, 0.043 mmol) in a mixture of concentrated hydrochloric acid (20 ml) and dimethyl sulfoxide (7 ml) was refluxed for 6 hours under heating. The reaction mixture was made basic with 28% aqueous ammonia, and the resulting crystals were filtered, washed with water and the crude product was purified by thin-layer chromatography to give the subject compound (6 mg, yield 35%).

Workup

  1. temperaturewas refluxed for 6 hours
  2. temperatureunder heating
  3. filtrationthe resulting crystals were filtered
  4. washwashed with water
  5. customthe crude product was purified by thin-layer chromatography

Sources & evidence

ORD record
ord-fbc4baa386e94f25b625c230b25880ce
Source dataset
uspto-grants-2001_12
Patent number
US06329381B1

Reaction notes

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