4,5-Dihydro-2-thiazolamine → HCID 70519458, compound

HRID 637659Notes

Reaction equation

HRID 637659 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][CH2:21][CH2:22][N:23]=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[S:20][CH2:21][CH2:22][N:23]=1

Participants

4

Reactant 2

HCID 156894,5-Dihydro-2-thiazolamineHCID 2474662-[1-(2,4-dioxo-3,4-dihydropyrimidin-1(2h)-yl)-2-oxoethoxy]-3-hydroxypropanal

Product 1

HCID 70519458HCID 70519458, compoundYield 28.7%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

[R-(R*, R*)]-α-(1-Formyl-2-hydroxyethoxy)-3,4dihydro-2,4-dioxo-1(2H)-pyrimidineacetaldehyde, (uridinedialdehyde), (2.4 g) was dissolved in water (10 ml). To the solution was added 2-amino-2-thiazoline (1.2 g). The mixture was stirred at ambient temperature overnight. An insoluble material was filtered off. The filtrate was evaporated in vacuo. The residue was triturated with acetone to give 1-[(2R, 6R)-3,5-dihydroxy-6-hydroxymethyl-4-(2-thiazolin-2-yl)morpholin-2-yl]uracil (0.98 g).

Workup

  1. filtrationAn insoluble material was filtered off
  2. customThe filtrate was evaporated in vacuo
  3. customThe residue was triturated with acetone

Sources & evidence

ORD record
ord-377cb7c30ca0490ab47f300c2fa9a9a9
Source dataset
uspto-grants-1985_12
Patent number
US04558047

Reaction notes

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