Water → (2-Amino-6-chloropyrimidin-4-yl)methanol

HRID 16431Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 16431
[NH2:1][C:2]1[N:7]=[C:6]([C:8](OC)=[O:9])[CH:5]=[C:4]([Cl:12])[N:3]=1.[BH4-].[Na+].C(OCC)(=O)C.O>C(O)C>[NH2:1][C:2]1[N:7]=[C:6]([CH2:8][OH:9])[CH:5]=[C:4]([Cl:12])[N:3]=1

Komponenten

6

Edukt 4

HCID 962WaterHCID 8857Ethyl AcetateHCID 239687Methyl 2-amino-6-chloropyrimidine-4-carboxylateHCID 4311764Sodium borohydride

Produkt 1

HCID 17979299(2-Amino-6-chloropyrimidin-4-yl)methanol

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel

Versuchsvorschrift

10.5 g (55.97 mmol) of methyl 2-amino-6-chloropyrimidine-4-carboxylate (prepared according to G. Doyle Daves, Fred Baiocchi, Roland K. Robins, and C. C. Cheng, J. Org. Chem., 26 (1961), 2755-2763) are initially charged in 450 ml of ethanol. 21.17 g (559.74 mmol) of sodium borohydride are added, and the mixture is stirred at room temperature for 2 hours. 500 ml of ethyl acetate and 500 ml of water are added, and the solution is stirred for 30 minutes. The phases are separated and the aqueous phase is extracted three times with ethyl acetate (in each case 100 ml). The combined organic phases are washed with saturated aqueous sodium chloride solution, dried with anhydrous magnesium sulfate and concentrated. This gives 7.21 g (85% of theory) of product.

Aufarbeitung

  1. stirringthe solution is stirred for 30 minutes
  2. customThe phases are separated
  3. extractionthe aqueous phase is extracted three times with ethyl acetate (in each case 100 ml)
  4. washThe combined organic phases are washed with saturated aqueous sodium chloride solution
  5. dry with materialdried with anhydrous magnesium sulfate
  6. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-fb2e5cdb8bf1472e836aa1162ff21f83
Quelldatensatz
uspto-grants-2010_06
Patentnummer
US07737153B2

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