Ethanolamine → 2-[[6-(1H-benzimidazol-1-yl)-9H-purin-2-yl]amino]ethanol

HRID 1453564Notes

Reaction equation

HRID 1453564 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.[CH2:20]([CH2:22][NH2:23])[OH:21]>CS(C)=O>[N:1]1([C:10]2[N:18]=[C:17]([NH:23][CH2:22][CH2:20][OH:21])[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 700EthanolamineHCID 178478376HCID 178478376, compound

Product 1

HCID 1785212912-[[6-(1H-benzimidazol-1-yl)-9H-purin-2-yl]amino]ethanol

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
120 °C

Procedure

210 mg of product obtained in stage 1 above are mixed with 2 ml of DMSO and 0.3 ml of ethanolamine, and the mixture is then heated at 120° C. for approximately 48 hours with stirring. 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-methanol (5-5). Partial drying and drying under vacuum at 50° C. are carried out. 118 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-methanol (5-5)
  5. customPartial drying
  6. customdrying under vacuum at 50° C.

Sources & evidence

ORD record
ord-a58efb2ae4bc439bb5b28921a6846364
Source dataset
uspto-grants-2009_01
Patent number
US07476670B2

Reaction notes

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