Adenine → HCID 21765788, compound

HRID 893611Notes

Reaction equation

HRID 893611 reaction equation
[N:1]1[C:9]([NH2:10])=[C:8]2[C:4]([N:5]=[CH:6][NH:7]2)=[N:3][CH:2]=1.C([O-])([O-])=O.[K+].[K+].C1OCCOCCOCCOCCOCCOC1.[CH3:35][O:36][CH:37]([O:44][CH3:45])[C@@H:38]1[O:42][CH2:41][C@@H:40](O)[CH2:39]1.CC1C=CC(S([O-])(=O)=O)=CC=1>CN(C=O)C.CO>[CH3:35][O:36][CH:37]([O:44][CH3:45])[C@@H:38]1[O:42][CH2:41][C@H:40]([N:5]2[CH:6]=[N:7][C:8]3[C:4]2=[N:3][CH:2]=[N:1][C:9]=3[NH2:10])[CH2:39]1

Participants

7

Reactant 4

HCID 190AdenineHCID 11430Potassium CarbonateHCID 2855718-Crown-6HCID 86745953HCID 86745953, compound

Product 1

HCID 21765788HCID 21765788, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6228DimethylformamideSolvent2×

Procedure

To a flame-dried argon blanketed round bottom flask equipped with a magnetic stir bar and condenser was added adenine (2.14 g, 15.8 mmole), K2CO3 (4.37 g, 31.6 mmole), 18-crown-6 (417 mg, 1.58 mmole) and DMF (400 mL). This mixture was allowed to stir at room temperature for 30 minutes under a stream of argon. A solution of (3S-trans)-tetrahydro-5-(dimethoxymethyl)-3-furanol-4-methylbenzenesulfonate. Compound IV(e), (5.0 g, 15.8 mmole) in 100 mL DMF was then added dropwise to the stirring mixture; the resultant mixture was warmed to 80° C., and stirred at that temperature overnight. Filtration, followed by evaporation of DMF, afforded a solid residue. This material was passed through a silica gel pad using a 7% MeOH/93% CH2Cl2 solution as eluant. Fractions containing the desired product were collected and evaporated to yield 3.0 g (71%) of Compound VI as a white solid:

Workup

  1. customTo a flame-dried argon blanketed round bottom flask equipped with a magnetic stir bar and condenser
  2. stirringstirred at that temperature overnight
  3. filtrationFiltration
  4. customfollowed by evaporation of DMF
  5. customafforded a solid residue

Sources & evidence

ORD record
ord-d0c1201074924d09a70ab6973812be42
Source dataset
uspto-grants-1992_06
Patent number
US05126347

Reaction notes

Loading…