2-Aminopyrimidine → HCID 13421437, compound

HRID 637658Notes

Reaction equation

HRID 637658 reaction equation
[CH:1]([CH:3]([O:6][CH:7]([C:10]1[S:11][CH:12]=[C:13]([C:15](=[O:17])[NH2:16])[N:14]=1)[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]([C:10]2[S:11][CH:12]=[C:13]([C:15](=[O:17])[NH2:16])[N:14]=2)[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 86740544HCID 86740544, compound

Product 1

HCID 13421437HCID 13421437, compoundYield 99.7%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

[R-(R*, R*)]-α-(1-Formyl-2-hydroxyethoxy)-4-carbamoyl-2-1,3-thiazoleacetaldehyde (1.10 g) was dissolved in water (30 ml). To the solution was added 2-aminopyrimidine (0.41 g). The mixture was stirred at ambient temperature for five hours to give a clear solution. The solution was lyophilized to give 2-[(2R, 6R)-3,5-dihydroxy-6-hydroxymethyl-4-(2-pyrimidinyl)morpholin-2-yl]-4-carbamoylthiazole (1.50 g).

Workup

  1. customto give a clear solution

Sources & evidence

ORD record
ord-271030f2a8994e3d8df56b824251193b
Source dataset
uspto-grants-1985_12
Patent number
US04558047

Reaction notes

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