2-[1-(2,4-dioxo-3,4-dihydropyrimidin-1(2h)-yl)-2-oxoethoxy]-3-hydroxypropanal → HCID 178516512, compound

HRID 637654Notes

Reaction equation

HRID 637654 reaction equation
[CH:1]([CH:3]([O:6][CH:7]([N:10]1[CH:15]=[CH:14][C:13](=[O:16])[NH:12][C:11]1=[O:17])[CH:8]=[O:9])[CH2:4][OH:5])=[O:2].[NH2:18][C:19]1[N:23]=[CH:22][NH:21][N:20]=1>CO.O>[OH:9][CH:8]1[C@H:7]([N:10]2[CH:15]=[CH:14][C:13](=[O:16])[NH:12][C:11]2=[O:17])[O:6][C@H:3]([CH2:4][OH:5])[CH:1]([OH:2])[N:18]1[C:19]1[N:23]=[CH:22][NH:21][N:20]=1

Participants

5

Reactant 2

HCID 2474662-[1-(2,4-dioxo-3,4-dihydropyrimidin-1(2h)-yl)-2-oxoethoxy]-3-hydroxypropanalHCID 178418311HCID 178418311, compound

Product 1

HCID 178516512HCID 178516512, compoundYield 95.9%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

[R-(R*, R*)]-α-(1-Formyl-2-hydroxyethoxy)-3,4-dihydro-2,4-dioxo-1(2H)-pyrimidineacetaldehyde, (uridinedialdehyde), (4.84 g) was dissolved in a mixture of methanol (100 ml) and water (100 ml). To the solution was added 3-amino-1H-1,2,4-triazole (1.68 g). The mixture was stirred at ambient temperature for five hours and evaporated in vacuo. The residue was triturated with acetone to give 1-[(2R, 6R)-3,5-dihydroxy-6-hydroxymethyl-4-(1,2,4-triazol-3-yl)morpholin-2-yl]uracil (6.25 g).

Workup

  1. customevaporated in vacuo
  2. customThe residue was triturated with acetone

Sources & evidence

ORD record
ord-a5c4179bbb7c4576a6f79f551dd16721
Source dataset
uspto-grants-1985_12
Patent number
US04558047

Reaction notes

Loading…