Phenol → HCID 178508848, compound

HRID 465719Notes

Reaction equation

HRID 465719 reaction equation
CC(C)([O-])C.[K+].[C:7]1([OH:13])[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1.[NH2:14][C:15]1[N:23]=[C:22]2[C:18]([NH:19][CH:20]=[N:21]2)=[C:17](Cl)[N:16]=1>CS(C)=O>[NH2:14][C:15]1[N:23]=[C:22]2[C:18]([N:19]=[CH:20][NH:21]2)=[C:17]([O:13][C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=2)[N:16]=1

Participants

5

Reactant 3

HCID 996PhenolHCID 53603492-Amino-6-chloropurineHCID 23665647Potassium tert-butoxide

Product 1

HCID 178508848HCID 178508848, compoundYield 22%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

Potassium t-butoxide (J. T. Baker, 7.3 g, 64.8 mmol) was added to a solution of phenol (Mallinckrodt, 15.2 g, 162 mmol) in 50 mL anhydrous DMSO. After stirring for 30 minutes, 2-amino-6-chloropurine (Sigma, lot #69F4064. 5.5 g, 32.4 mmol) was added and the mixture stirred for 6 days at 100° C. The reaction was poured onto ice and extracted with EtOAc. The solvents were removed in vacuo and the resultant oil applied to a silica gel column. Elution with CHCl3 /MeOH (95:5, v/v) followed by combination and evaporation of appropriate fractions gave 1.6 g (7.0 mmol, 22%) of product. mp=228° C.

Workup

  1. stirringthe mixture stirred for 6 days at 100° C
  2. additionThe reaction was poured onto ice
  3. extractionextracted with EtOAc
  4. customThe solvents were removed in vacuo
  5. washElution with CHCl3 /MeOH (95:5
  6. customv/v) followed by combination and evaporation of appropriate fractions

Sources & evidence

ORD record
ord-8e45907d42774741ad606c378e36be0b
Source dataset
uspto-grants-1992_10
Patent number
US05153318

Reaction notes

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