2-Aminopyrimidine → HCID 13421427, compound

HRID 637653Notes

Reaction equation

HRID 637653 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:24]=[CH:23][CH:22]=[CH:21][N:20]=1>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:24]=[CH:23][CH:22]=[CH:21][N:20]=1

Participants

4

Reactant 2

HCID 79782-AminopyrimidineHCID 2474662-[1-(2,4-dioxo-3,4-dihydropyrimidin-1(2h)-yl)-2-oxoethoxy]-3-hydroxypropanal

Product 1

HCID 13421427HCID 13421427, compoundYield 99.7%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

[R-(R*, R*)]-α-(1-Formyl-2-hydroxyethoxy)-3,4-dihydro-2,4-dioxo-1(2H)-pyrimidineacetaldehyde, (uridinedialdehyde), (6.05 g) was dissolved in water (25 ml). To the solution was added 2-aminopyrimidine (2.38 g). The mixture was stirred at ambient temperature for eight hours to give a clear solution. The solution was lyophilized to give white powder of 1-[(2R, 6R)-3,5-dihydroxy-6-hydroxymethyl-4-(2-pyrimidinyl)morpholin-2-yl]uracil (8.40 g).

Workup

  1. customto give a clear solution

Sources & evidence

ORD record
ord-07c01c9157384e64b73ae46f292cc4d2
Source dataset
uspto-grants-1985_12
Patent number
US04558047

Reaction notes

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