3-Amino-5-methylisoxazole → HCID 13421431, compound

HRID 637655Notes

Reaction equation

HRID 637655 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[CH:23]=[C:22]([CH3:24])[O: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[CH:23]=[C:22]([CH3:24])[O:21][N:20]=1

Participants

5

Reactant 2

HCID 661723-Amino-5-methylisoxazoleHCID 2474662-[1-(2,4-dioxo-3,4-dihydropyrimidin-1(2h)-yl)-2-oxoethoxy]-3-hydroxypropanal

Product 1

HCID 13421431HCID 13421431, compoundYield 74.7%

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), (4.0 g) was dissolved in a mixture of methanol (30 ml) and water (30 ml). To the solution was added 3-amino-5-methylisoxazole (1.62 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-(5-methylisoxazol-3-yl)morpholin-2-yl]uracil (4.2 g).

Workup

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

Sources & evidence

ORD record
ord-1ff5de46fb254e2ea1ca25d18d1e0f86
Source dataset
uspto-grants-1985_12
Patent number
US04558047

Reaction notes

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