Guanine → HCID 136387276, compound

HRID 637657Notes

Reaction equation

HRID 637657 reaction equation
[CH:1]([CH:3]([O:6][CH:7]([N:10]1[CH:18]=[N:17][C:16]2[C:15](=[O:19])[NH:14][CH:13]=[N:12][C:11]1=2)[CH:8]=[O:9])[CH2:4][OH:5])=[O:2].[NH:20]1[C:29](=[O:30])[C:28]2[NH:27][CH:26]=[N:25][C:24]=2[N:23]=[C:21]1[NH2:22]>CO.O>[OH:9][CH:8]1[C@H:7]([N:10]2[CH:18]=[N:17][C:16]3[C:15](=[O:19])[NH:14][CH:13]=[N:12][C:11]2=3)[O:6][C@H:3]([CH2:4][OH:5])[CH:1]([OH:2])[N:22]1[C:21]1[NH:20][C:29](=[O:30])[C:28]2[NH:27][CH:26]=[N:25][C:24]=2[N:23]=1

Participants

5

Reactant 2

HCID 135398634GuanineHCID 135428309HCID 135428309, compound

Product 1

HCID 136387276HCID 136387276, compoundYield 105.5%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

[R-(R*, R*)]-α-(1-Formyl-2-hydroxyethoxy)-1,6-dihydro-6-oxo-9H-purine-9-acetaldehyde, (inosinedialdehyde), (1.33 g) was dissolved in a mixture of methanol (300 ml) and water (300 ml). To the solution was added guanine (0.76 g). The mixture was stirred at ambient temperature for three days and filtered. The filtrate was evaporated in vacuo at 35° C. The residue was triturated with acetone to give 9-[(2R, 6R)-3,5-dihydroxy-6-hydroxymethyl-4-(2-hypoxanthinyl)morpholin-2-yl]hypoxanthine (2.20 g).

Workup

  1. filtrationfiltered
  2. customThe filtrate was evaporated in vacuo at 35° C
  3. customThe residue was triturated with acetone

Sources & evidence

ORD record
ord-865881b1beba48d4ab0b2355399a512e
Source dataset
uspto-grants-1985_12
Patent number
US04558047

Reaction notes

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