Purine → HCID 178420486, compound

HRID 716859Notes

Reaction equation

HRID 716859 reaction equation
[N:1]1[CH:9]=[C:8]2[C:4]([N:5]=[CH:6][NH:7]2)=[N:3][CH:2]=1.ClC1N=CN=C2C=1NC=N2.[NH2:20][C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1.C([O-])([O-])=O.[K+].[K+]>O1CCOCC1>[C:21]1([NH:20][C:9]2[N:1]=[CH:2][N:3]=[C:4]3[C:8]=2[N:7]=[CH:6][NH:5]3)[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1

Participants

6

Reactant 4

HCID 1044PurineHCID 6115AnilineHCID 11430Potassium CarbonateHCID 53592776-Chloropurine

Product 1

HCID 178420486HCID 178420486, compound

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

The general procedure for the synthesis of purine derivatives is depicted in FIG. 1. The initial compound 6-chloropurine (1.0 eq.) was mixed with aniline (1.20 eq.) and K2CO3 (2.5 eq.) in 50.0 ml dioxane. The resultant mixture was charged in 100 mL round bottom flask with a stirring bar. The mixture was refluxed overnight and monitored by TLC. After the reaction finished, the solvent was removed and the remaining residue was extracted by ethyl acetate. After removing the solvent, the resultant crude product was purified by silica gel column chromatography eluting with CH2Cl2/MeOH (5%) to provide pure titled compound.

Workup

  1. temperatureThe mixture was refluxed overnight
  2. customthe solvent was removed
  3. extractionthe remaining residue was extracted by ethyl acetate
  4. customAfter removing the solvent
  5. customthe resultant crude product was purified by silica gel column chromatography
  6. washeluting with CH2Cl2/MeOH (5%)

Sources & evidence

ORD record
ord-f2e117a9e6a742a3af4dcf7ebec7395a
Source dataset
uspto-grants-2015_11
Patent number
US09193711B2

Reaction notes

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