Potassium Carbonate → Methyl 4-[(2-amino-6-chloro-9H-purin-9-yl)methyl]benzoate

HRID 2352010Notes

Reaction equation

HRID 2352010 reaction equation
[NH2:1][C:2]1[N:10]=[C:9]2[C:5]([NH:6][CH:7]=[N:8]2)=[C:4]([Cl:11])[N:3]=1.[CH3:12][O:13][C:14](=[O:23])[C:15]1[CH:20]=[CH:19][C:18]([CH2:21]Br)=[CH:17][CH:16]=1.C(=O)([O-])[O-].[K+].[K+].CO.C(Cl)(Cl)Cl>CN(C=O)C>[NH2:1][C:2]1[N:10]=[C:9]2[C:5]([N:6]=[CH:7][N:8]2[CH2:21][C:18]2[CH:17]=[CH:16][C:15]([C:14]([O:13][CH3:12])=[O:23])=[CH:20][CH:19]=2)=[C:4]([Cl:11])[N:3]=1

Participants

6

Reactant 4

HCID 11430Potassium CarbonateHCID 256687Methyl 4-(bromomethyl)benzoateHCID 53603492-Amino-6-chloropurineHCID 21584188Chloroform methanol

Product 1

HCID 14182432Methyl 4-[(2-amino-6-chloro-9H-purin-9-yl)methyl]benzoate

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 2-amino-6-chloropurine (5 g, 0.029 mol), 4-(bromomethyl)benzoic acid methyl ester (6.7 g, 0.029 mol), and potassium carbonate (4.0 g, 0.029 mol) in dry DMF (75 ml) is stirred at room temperature for three days. The reaction mixture is filtered and the filtrate is evaporated to near dryness under vacuum. Water is added and the precipitate is collected by filtration to give a mixture of 7- and 9-substituted products (10.5 g). A sample of pure 9-isomer, i.e., 2-amino-9-[(4-carbomethoxyphenyl)methyl)-6-chloropurine, (mp=150°-155° C. softens, 183°-185° C. melts) is prepared by chromatography on silica gel with 5% methanol/chloroform as the eluting solvent to separate it from the slower moving 7-isomer.

Workup

  1. filtrationThe reaction mixture is filtered
  2. customthe filtrate is evaporated
  3. additionWater is added
  4. filtrationthe precipitate is collected by filtration
  5. customto give
  6. customto separate it from the

Sources & evidence

ORD record
ord-049a333426094ddfb66dbbbecb67461a
Source dataset
uspto-grants-1989_10
Patent number
US04874862

Reaction notes

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