Acetone → 2-amino-9-[6-(hydroxymethyl)-2,2-dimethyl-3a,4,6,6a-tetrahydrofuro[3,4-d][1,3]dioxol-4-yl]-3H-purin-6-one

HRID 1921907Notes

Reaction equation

HRID 1921907 reaction equation
[C@@H:1]1([N:10]2[C:20]3[N:19]=[C:17]([NH2:18])[NH:16][C:14](=[O:15])[C:13]=3[N:12]=[CH:11]2)[O:9][C@H:6]([CH2:7][OH:8])[C@@H:4]([OH:5])[C@H:2]1[OH:3].[NH4+].[OH-].[CH3:23][C:24]([CH3:26])=O>>[NH2:18][C:17]1[NH:16][C:14](=[O:15])[C:13]2[N:12]=[CH:11][N:10]([CH:1]3[CH:2]4[CH:4]([O:5][C:24]([CH3:26])([CH3:23])[O:3]4)[CH:6]([CH2:7][OH:8])[O:9]3)[C:20]=2[N:19]=1

Participants

4

Reactant 3

HCID 180AcetoneHCID 14923Ammonium HydroxideHCID 135398635Guanosine

Product 1

HCID 1354241802-amino-9-[6-(hydroxymethyl)-2,2-dimethyl-3a,4,6,6a-tetrahydrofuro[3,4-d][1,3]dioxol-4-yl]-3H-purin-6-oneYield 92%

Conditions

Temperature
0 °C

Procedure

To a slurry of guanosine (0.25 g, 1.0 eq) (10) and acetone (15 mL) at room temperature was added 70% HClO4 (0.103 mL, 1.35 eq). The reaction was stirred for approximately 70 minutes, at which time it was clear and colorless. The reaction was then cooled to 0° C. in an ice/water bath and concentrated NH4OH (0.167 mL, 1.41 eq) was added causing the formation of a milky white, gelatinous precipitate. The precipitate was collected on filter paper, resulting in a white papery solid that was dried at reduced pressure and ambient temperature for approximately 1 hour yielding 11 (0.262 g, 92%).

Workup

  1. customThe precipitate was collected
  2. filtrationon filter paper
  3. customresulting in a white papery solid
  4. customthat was dried at reduced pressure and ambient temperature for approximately 1 hour

Sources & evidence

ORD record
ord-77f195e0ee6348b0bfc8af6275f10ac7
Source dataset
uspto-grants-2012_05
Patent number
US08173797B2

Reaction notes

Loading…