Potassium Carbonate → HCID 14236876, compound

HRID 2290543Notes

Reaction equation

HRID 2290543 reaction equation
[C:1]([O:9][CH2:10][C:11]1([CH2:26][O:27][C:28](=[O:35])[C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=2)[CH2:13][CH:12]1[CH2:14]OS(C1C=CC(C)=CC=1)(=O)=O)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[NH2:36][C:37]1[N:45]=[C:44]2[C:40]([NH:41][CH:42]=[N:43]2)=[C:39]([Cl:46])[N:38]=1.C([O-])([O-])=O.[K+].[K+]>CN(C)C=O.C(Cl)(Cl)Cl.CO.O>[NH2:36][C:37]1[N:45]=[C:44]2[C:40]([N:41]=[CH:42][N:43]2[CH2:14][CH:12]2[CH2:13][C:11]2([CH2:10][O:9][C:1](=[O:8])[C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=2)[CH2:26][O:27][C:28](=[O:35])[C:29]2[CH:30]=[CH:31][CH:32]=[CH:33][CH:34]=2)=[C:39]([Cl:46])[N:38]=1

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 53603492-Amino-6-chloropurineHCID 14236875HCID 14236875, compound

Product 1

HCID 14236876HCID 14236876, compoundYield 53.5%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolvent2×HCID 21866399Chloroform methanol waterSolvent

Procedure

A solution of 3.36 g (6.8 mmoles) of 1,1-bis(benzoyloxymethyl)-2-p-toluenesulfonyloxymethylcyclopropane in 15 ml of dry DMF (dimethylformamide) was added to a mixture of 1.37 g (8.2 mmoles) of 2-amino-6-chloropurine and 1.2 g (8.8 mmoles) of K2CO3 in 20 ml of DMF. The mixture was heated to 60° and stirred for 4 hours. The reaction was monitored by TLC in chloroform-methanol-water (95:5:0.3) Rf 0.15, 0.9 (starting material), 0.4, 0.6 (Product). The reaction mixture was concentrated and the residue dissolved in 60 ml of CHCl3 --MeOH (1:1). About 20 ml of silica gel was added and the mixture was concentrated to dryness. The residue was added to the top of a 200 ml silica gel column and chromatographed in CMW (chloroform-methanol-water) (97.5:2.5:0.15). Fractions containing the two products (the 9 and 7 isomers) were cooled separately and concentrated to give 1.79 g (53%) of the title compound and 170 mg (5.1%) of the 7-isomer.

Workup

  1. temperatureThe mixture was heated to 60°
  2. concentrationThe reaction mixture was concentrated
  3. dissolutionthe residue dissolved in 60 ml of CHCl3 --MeOH (1:1)
  4. additionAbout 20 ml of silica gel was added
  5. concentrationthe mixture was concentrated to dryness
  6. additionThe residue was added to the top of a 200 ml silica gel column
  7. customchromatographed in CMW (chloroform-methanol-water) (97.5:2.5:0.15)
  8. additionFractions containing the two products (the 9 and 7 isomers)
  9. temperaturewere cooled separately
  10. concentrationconcentrated

Sources & evidence

ORD record
ord-d92bead6e9dc4284bf059a890b3fd613
Source dataset
uspto-grants-1986_10
Patent number
US04617304

Reaction notes

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