Pyridine → 1-Methyl-3-phenyl-7-(2-cyano-benzyl)-8-chloro-xanthine

HRID 633680Notes

Reaction equation

HRID 633680 reaction equation
[CH3:1][N:2]1[C:11](=[O:12])[C:10]2[N:9]([CH2:13][C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=3[C:20]#[N:21])[C:8]([Cl:22])=[N:7][C:6]=2[NH:5][C:3]1=[O:4].[C:23]1(OB(O)O)[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1.N1C=CC=CC=1>C(Cl)Cl.C([O-])(=O)C.[Cu+2].C([O-])(=O)C>[CH3:1][N:2]1[C:11](=[O:12])[C:10]2[N:9]([CH2:13][C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=3[C:20]#[N:21])[C:8]([Cl:22])=[N:7][C:6]=2[N:5]([C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)[C:3]1=[O:4]

Participants

6

Reactant 3

HCID 1049PyridineHCID 78412Phenyl dihydrogen orthoborate2×HCID 575145401-Methyl-7-(2-cyano-benzyl)-8-chloro-xanthine

Product 1

HCID 667540151-Methyl-3-phenyl-7-(2-cyano-benzyl)-8-chloro-xanthine

Reagents, catalysts & solvents 2

HCID 8895Cupric acetateCatalystHCID 6344DichloromethaneSolvent

Procedure

A mixture of 829 mg of 1-methyl-7-(2-cyano-benzyl)-8-chloro-xanthine, 640 mg of phenylboric acid, 509 mg of anhydrous copper acetate and 0.43 ml of pyridine in 20 ml methylene chloride is stirred for four days at ambient temperature in the presence of 100 mg of 4 Å molecular sieves. Then another 320 mg of phenylboric acid are added and the reaction mixture is stirred for another day at ambient temperature. For working up the mixture is filtered through talc and washed with ethyl acetate. The filtrate is evaporated down and chromatographed through a silica gel column with cyclohexane/ethyl acetate (7:3 to 1:1) as eluant.

Workup

  1. stirringthe reaction mixture is stirred for another day at ambient temperature
  2. filtrationis filtered through talc
  3. washwashed with ethyl acetate
  4. customThe filtrate is evaporated down
  5. customchromatographed through a silica gel column with cyclohexane/ethyl acetate (7:3 to 1:1) as eluant

Sources & evidence

ORD record
ord-bcda929abd3f446c8c21674c0823514b
Source dataset
uspto-grants-2016_04
Patent number
US09321791B2

Reaction notes

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