1,3,4-Thiadiazol-2-amine → HCID 13421424, compound

HRID 637651Notes

Reaction equation

HRID 637651 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[S:20][CH:21]=[N:22][N:23]=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[S:20][CH:21]=[N:22][N:23]=1

Participants

5

Reactant 2

HCID 199091,3,4-Thiadiazol-2-amineHCID 2474662-[1-(2,4-dioxo-3,4-dihydropyrimidin-1(2h)-yl)-2-oxoethoxy]-3-hydroxypropanal

Product 1

HCID 13421424HCID 13421424, compoundYield 88.4%

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), (2.42 g) was dissolved in a mixture of methanol (50 ml) and water (50 ml). To the solution was added 2-amino-1,3,4-thiadiazole (1.00 g). The mixture was stirred at ambient temperature for four hours and evaporated in vacuo. The residue was triturated with acetone to give 1-[(2R, 6R)-3,5-dihydroxy-6-hydroxymethyl-4-(1,3,4-thiadiazol-2-yl)morpholin-2-yl]-uracil (3.0 g).

Workup

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

Sources & evidence

ORD record
ord-3fbd31f43acd47c1b8cb1096a47c49e9
Source dataset
uspto-grants-1985_12
Patent number
US04558047

Reaction notes

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