Diethanolamine → 2,2'-[[6-(1H-benzimidazol-1-yl)-9H-purin-2-yl]imino]bisethanol

HRID 1453570Notes

Reaction equation

HRID 1453570 reaction equation
[N:1]1([C:10]2[N:18]=[C:17](Cl)[N:16]=[C:15]3[C:11]=2[N:12]=[CH:13][NH:14]3)[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[CH:2]1.[NH:20]([CH2:24][CH2:25][OH:26])[CH2:21][CH2:22][OH:23]>CS(C)=O>[N:1]1([C:10]2[N:18]=[C:17]([N:20]([CH2:24][CH2:25][OH:26])[CH2:21][CH2:22][OH:23])[N:16]=[C:15]3[C:11]=2[N:12]=[CH:13][NH:14]3)[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[CH:2]1

Participants

4

Reactant 2

HCID 8113DiethanolamineHCID 178478376HCID 178478376, compound

Product 1

HCID 1785213232,2'-[[6-(1H-benzimidazol-1-yl)-9H-purin-2-yl]imino]bisethanolYield 7,042.7%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
120 °C

Procedure

200 mg of product obtained in stage 1 above are mixed with 3 ml of DMSO and 0.388 mg (5 equivalents) of diethanolamine, and the mixture is then heated at 120° C. for approximately 48 hours. The mixture is allowed to return to ambient temperature. Purification is carried out by chromatography on silica with a CH2Cl2-MeOH—NH4OH: 90-9-1 mixture for eluent. Evaporation is carried out and a paste is formed in methylene chloride. Partial drying and drying under vacuum at 50° C. are carried out. 88.2 mg of expected product are obtained.

Workup

  1. customto return to ambient temperature
  2. customPurification
  3. customEvaporation
  4. customa paste is formed in methylene chloride
  5. customPartial drying
  6. customdrying under vacuum at 50° C.

Sources & evidence

ORD record
ord-2320affbd00c44ea82df282fee9937ca
Source dataset
uspto-grants-2009_01
Patent number
US07476670B2

Reaction notes

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