4-Chloro-2-(methylthio)pyrimidine-5-carboxylic acid ethyl ester → HCID 54279591, compound

HRID 231776Notes

Reaction equation

HRID 231776 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[C:7](Cl)=[N:8][C:9]([S:12][CH3:13])=[N:10][CH:11]=1)=[O:5])[CH3:2].[OH:15][CH:16]([CH2:24][OH:25])[CH2:17][N:18]1[CH2:23][CH2:22][NH:21][CH2:20][CH2:19]1>O1CCOCC1>[CH2:1]([O:3][C:4]([C:6]1[C:7]([N:21]2[CH2:20][CH2:19][N:18]([CH2:17][CH:16]([OH:15])[CH2:24][OH:25])[CH2:23][CH2:22]2)=[N:8][C:9]([S:12][CH3:13])=[N:10][CH:11]=1)=[O:5])[CH3:2]

Participants

4

Reactant 2

HCID 800084-Chloro-2-(methylthio)pyrimidine-5-carboxylic acid ethyl esterHCID 1110023-(Piperazin-1-yl)propane-1,2-diol

Product 1

HCID 54279591HCID 54279591, compound

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

Grams 4.6 of 2-methylthio-4-chloropyrimidine-5-carboxylic acid ethyl ester and 6.4 g of 1-(2,3-dihydroxypropyl)piperazine in 50 ml dioxane were refluxed for 30 minutes. The mixture was cooled and settled, then the solvent was evaporated and the dried residue purified on column eluting with chloroform:methanol (9:1). Grams 4.8 of 2-methylthio-4-[4-(2,3-dihydroxypropyl)piperazin-1-yl]pyrimidine-5-carboxylic acid ethyl ester as an oil, were obtained.

Workup

  1. temperatureThe mixture was cooled
  2. customthe solvent was evaporated
  3. customthe dried residue purified on column
  4. washeluting with chloroform:methanol (9:1)

Sources & evidence

ORD record
ord-ec65ab8427454d47a1e4c69debec223c
Source dataset
uspto-grants-1989_07
Patent number
US04849422

Reaction notes

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