Adenine → Benzoic acid 2-(6-amino-purin-9-yl)-5-[2-(diethoxy-phosphoryl)-vinyl]-tetrahydro-furan-3-yl ester

HRID 2191018Notes

Reaction equation

HRID 2191018 reaction equation
[CH2:1]([O:3][P:4]([CH:9]=[CH:10][CH:11]1[CH2:15][CH:14](C(=O)C2C=CC=CC=2)[CH:13](C(=O)C2C=CC=CC=2)[O:12]1)(=[O:8])[O:5][CH2:6][CH3:7])[CH3:2].[N:32]1[C:40]([NH2:41])=[C:39]2[C:35]([N:36]=[CH:37][NH:38]2)=[N:34][CH:33]=1.Cl[Sn](Cl)(Cl)Cl.[C:47]([O-:50])(O)=[O:48].[Na+].[CH3:52][C:53]#N>O>[NH2:41][C:40]1[N:32]=[CH:33][N:34]=[C:35]2[C:39]=1[N:38]=[CH:37][N:36]2[CH:13]1[CH:14]([O:50][C:47](=[O:48])[C:53]2[CH:52]=[CH:15][CH:11]=[CH:10][CH:9]=2)[CH2:15][CH:11]([CH:10]=[CH:9][P:4]([O:3][CH2:1][CH3:2])([O:5][CH2:6][CH3:7])=[O:8])[O:12]1

Participants

7

Reactant 5

HCID 190AdenineHCID 6342Acetonitrile2×HCID 24287Tin tetrachlorideHCID 516892Sodium BicarbonateHCID 86641113[2-(4,5-Dibenzoyl-tetrahydro-furan-2-yl)-vinyl]-phosphonic acid diethyl ester

Product 1

HCID 72247311Benzoic acid 2-(6-amino-purin-9-yl)-5-[2-(diethoxy-phosphoryl)-vinyl]-tetrahydro-furan-3-yl esterYield 48%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Compound 9.8 (430 mg, 0.907 mmol) and adenine (135 mg, 1.0 mmol) was dissolved in 10 mL anhydrous CH3CN. The mixture was treated with SnCl4 (0.234 mL, 2.0 mmol) and stirred at r.t. for 20 h. The mixture was cooled to 0° C., treated with NaHCO3 (2 g), water (2 mL), and stirred for 2 h. The mixture was diluted with CH3CN, filtered, and concentrated under reduced pressure. The residue was subjected to a silica gel column chromatography eluting with EtOAc to 20% MeOH in EtOAc to yield compound 12.1 (210 mg, 48% yield).

Workup

  1. temperatureThe mixture was cooled to 0° C.
  2. stirringstirred for 2 h
  3. filtrationfiltered
  4. concentrationconcentrated under reduced pressure
  5. washeluting with EtOAc to 20% MeOH in EtOAc

Sources & evidence

ORD record
ord-7b1e52c4587943f6bcd7b638faccb524
Source dataset
uspto-grants-2012_12
Patent number
US08324179B2

Reaction notes

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