Dimethyl Sulfoxide → 9H-Purin-6-ol, 2-((phenylmethyl)amino)-

HRID 570989Notes

Reaction equation

HRID 570989 reaction equation
NC[C:3]1[C:8]([CH2:9][NH:10][C:11]2[NH:12][C:13](=[O:20])[C:14]3[NH:15][CH:16]=[N:17][C:18]=3[N:19]=2)=[CH:7][CH:6]=[CH:5][CH:4]=1.CS(C)=O.C(#N)C.C([O-])(=O)C.C([NH+](CC)CC)C>O>[CH2:9]([NH:10][C:11]1[NH:12][C:13](=[O:20])[C:14]2[NH:15][CH:16]=[N:17][C:18]=2[N:19]=1)[C:8]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 4

HCID 679Dimethyl Sulfoxide2×HCID 6342AcetonitrileHCID 11073729Triethyl ammonium acetateHCID 1363862616-Aminomethylbenzylguanine

Product 1

HCID 1354350909H-Purin-6-ol, 2-((phenylmethyl)amino)-

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Introduced into a 1.5 ml Eppendorf tube were 100 μl of a solution containing 10 mmol·l−1 of 6-aminomethylbenzylguanine in anhydrous dimethylsulfoxide (1 μmol) and 100 μl of a solution containing 10 mmol·l−1 of Tb(KR)-NHS in anhydrous dimethylsulfoxide (1 μmol). The mixture was stirred for one hour. The reaction was monitored by HPLC on a Merck Lichrospher RP °18, 5 μm, 125×4.6 column with a gradient of acetonitrile in water containing 25 mM of triethylammonium acetate.

Workup

  1. additionIntroduced into a 1.5 ml Eppendorf tube

Sources & evidence

ORD record
ord-d7fabe4ba8214f4b939b5ed3ea57d1a0
Source dataset
uspto-grants-2015_05
Patent number
US09024022B2

Reaction notes

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