Potassium Hydroxide → HCID 59835115, compound

HRID 271278Notes

Reaction equation

HRID 271278 reaction equation
[O:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[C:6]1[NH:14][C:13]([NH2:15])=[N:12][C:11]2[C:7]=1[N:8]=[CH:9][N:10]=2.[OH-].[K+].S(O[CH2:23][C@H:24]([CH3:33])[NH:25]C(OCCCC)=O)(=O)(=O)C.C(OC(OC(C)(C)C)=O)(OC(C)(C)C)=O>CS(C)=O.O>[NH2:25][C@@H:24]([CH3:33])[CH2:23][N:10]1[CH:9]=[N:8][C:7]2[C:11]1=[N:12][C:13]([NH2:15])=[N:14][C:6]=2[C:2]1[O:1][CH:5]=[CH:4][CH:3]=1

Participants

7

Reactant 4

HCID 14797Potassium HydroxideHCID 90495Di-tert-butyl dicarbonateHCID 86592468HCID 86592468, compoundHCID 1785082476-(furan-2-yl)-9H-purin-2-amine

Product 1

HCID 59835115HCID 59835115, compoundYield 51.9%

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 962WaterSolvent

Procedure

A solution of the 6-(2-furyl)-1H-purine-2-amine (0.1 g, 0.5 mmol) in DMSO was treated with freshly ground KOH (112 mg, 2 mmol), shaken for 10 min, treated with N-butoxycarbonyl-L-alaninol mesylate (316 mg, 3 mmol), shaken at 40° C. for a further 17 h, treated with di-tert-butyl dicarbonate (655 mg, 3 mmol), shaken for a further 30 min, diluted with H2O, extracted with EtOAc and the extracts dried (MgSO4), concentrated in vacuo and purified by chromatography [SiO2; (EtOAc)]. The resulting gelatinous solid was dissolved in MeOH (3 mL), treated with HCl solution (4-M in dioxan, 0.5 mL), stirred for 17 h, diluted with Et2O and filtered to give the title compound (67 mg, 45%) as a yellow solid.

Workup

  1. stirringshaken at 40° C. for a further 17 h
  2. stirringshaken for a further 30 min
  3. extractionextracted with EtOAc
  4. dry with materialthe extracts dried (MgSO4)
  5. concentrationconcentrated in vacuo
  6. custompurified by chromatography [SiO2; (EtOAc)]
  7. dissolutionThe resulting gelatinous solid was dissolved in MeOH (3 mL)
  8. additiontreated with HCl solution (4-M in dioxan, 0.5 mL)
  9. stirringstirred for 17 h
  10. additiondiluted with Et2O
  11. filtrationfiltered

Sources & evidence

ORD record
ord-4be7ea3a2cb149cf8b96460689feb988
Source dataset
uspto-grants-2008_11
Patent number
US07452894B2

Reaction notes

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