Methanol → Methyl 5-aminopyrimidine-2-carboxylate

HRID 1526615

Reaktionsgleichung

Reaktionsgleichung von HRID 1526615
[NH2:1][C:2]1[CH:3]=[N:4][C:5]([C:8]([OH:10])=[O:9])=[N:6][CH:7]=1.S(Cl)(Cl)=O.[CH3:15]O>C([O-])(O)=O.[Na+]>[NH2:1][C:2]1[CH:3]=[N:4][C:5]([C:8]([O:10][CH3:15])=[O:9])=[N:6][CH:7]=1

Komponenten

5

Edukt 3

HCID 887MethanolHCID 24386Thionyl ChlorideHCID 122159975-Aminopyrimidine-2-carboxylic Acid

Produkt 1

HCID 10654421Methyl 5-aminopyrimidine-2-carboxylateAusbeute 68 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 516892Sodium BicarbonateLösungsmittel

Versuchsvorschrift

A suspension of 5-aminopyrimidine-2-carboxylic acid (Goldenbridge Pharma, Inc.; 5.70 g, 41.0 mmol) in MeOH (120 mL) was cooled in an ice-water bath and treated dropwise with thionyl chloride (8.97 mL, 123 mmol). The resulting suspension was heated at reflux for 20 h and then concentrated to give a yellow solid. The solid was dissolved in saturated aqueous NaHCO3 (60 mL) and extracted into EtOAc using a Gregar Extractor. The extract was concentrated to give methyl 5-aminopyrimidine-2-carboxylate (4.26 g, 68% yield) as an off-white solid. 1H NMR (400 MHz, CDCl3): δ 8.32 (s, 2H), 4.35 (br s, 2H), 4.02 (s, 3H).

Aufarbeitung

  1. temperaturewas cooled in an ice-water bath
  2. temperatureThe resulting suspension was heated
  3. temperatureat reflux for 20 h
  4. concentrationconcentrated
  5. customto give a yellow solid
  6. extractionextracted into EtOAc using a Gregar Extractor
  7. concentrationThe extract was concentrated

Quellen und Nachweise

ORD-Eintrag
ord-4fd510a635314d1b8ce240a831f8fb8d
Quelldatensatz
uspto-grants-2015_07
Patentnummer
US09085576B2

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