N2 acetyl-9-(1,3-dibenzyloxy-2-propoxymethyl)guanine → N2 acetyl-9-(1,3-dihydroxy-2-propoxymethyl)guanine

HRID 65102

Reaction equation

HRID 65102 reaction equation
[N:1]#[N:2].[C:3]([NH:6][C:7]1[NH:8][C:9](=[O:37])[C:10]2[N:11]=[CH:12][N:13]([CH2:16][O:17][CH:18]([CH2:28][O:29]CC3C=CC=CC=3)[CH2:19][O:20]CC3C=CC=CC=3)[C:14]=2[N:15]=1)(=[O:5])[CH3:4].[H][H]>CO.O.[OH-].[OH-].[Pd+2]>[N:1]#[N:2].[C:3]([NH:6][C:7]1[NH:8][C:9](=[O:37])[C:10]2[N:11]=[CH:12][N:13]([CH2:16][O:17][CH:18]([CH2:19][OH:20])[CH2:28][OH:29])[C:14]=2[N:15]=1)(=[O:5])[CH3:4]

Participants

6

Reactant 2

HCID 136408872N2 acetyl-9-(1,3-dibenzyloxy-2-propoxymethyl)guanineHCID 178418361HCID 178418361, compound

Product 1

HCID 136408871N2 acetyl-9-(1,3-dihydroxy-2-propoxymethyl)guanineYield 44.5%

Reagents, catalysts & solvents 3

HCID 9942167Palladium hydroxideCatalystHCID 887MethanolSolventHCID 962WaterSolvent2×

Procedure

To a solution of N2 -acetyl-9-(1,3-dibenzyloxy-2-propoxymethyl)guanine (4.62 g, 9.67 mmol) in 150 ml of methanol plus 40 ml of water was added 20% palladium hydroxide on carbon as a slurry in 10 ml of water. The mixture was hydrogenated on a Parr hydrogenator at 60 psi of hydrogen for 38 hours then filtered through celite and concentrated to a white solid. Recrystallization from methanol/ethyl acetate gave 1.4 g of N2 -acetyl-9-(1,3-dihydroxy-2-propoxymethyl)guanine, mp 205°-208° C.

Workup

  1. filtrationthen filtered through celite
  2. concentrationconcentrated to a white solid
  3. customRecrystallization from methanol/ethyl acetate

Sources & evidence

ORD record
ord-1953368d239047448e95f7b75de50592
Source dataset
uspto-grants-1986_09
Patent number
US04612314

Linked notes

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