1,2-Dichloroethane → 4-amino-N-methylpyrimidine-5-carboxamide

HRID 1887704Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1887704
[NH2:1][C:2]1[C:7]([C:8]([OH:10])=O)=[CH:6][N:5]=[CH:4][N:3]=1.Cl.CN.C(Cl)CCl.C1C=CC2N(O)N=[N:24][C:22]=2C=1.CCN(C(C)C)C(C)C>CN(C=O)C>[NH2:1][C:2]1[C:7]([C:8]([NH:24][CH3:22])=[O:10])=[CH:6][N:5]=[CH:4][N:3]=1

Komponenten

7

Edukt 5

HCID 111,2-DichloroethaneHCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 12014404-Aminopyrimidine-5-carboxylic acidHCID 6364545Methylamine hydrochloride

Produkt 1

HCID 134684384-amino-N-methylpyrimidine-5-carboxamideAusbeute 85,5 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

To the mixture of 4-aminopyrimidine-5-carboxylic acid (0.75 g, 5.39 mmol), methylamine hydrogen chloride (0.44 g, 1.2 eq), EDC (1.67 g, 1.5 eq), HOBt (0.87 g, 1.2 eq) in DMF (20 mL) was added DIEA (3.8 mL, 4.0 eq). The mixture was stirred at room temperature overnight. The crude was concentrated and dissolved in EtOAc. It was washed with saturated NaHCO3 solution. The solvent was removed and the crude was purified by silica gel chromatography (0%˜20% MeOH/DCM) to obtain the desired product 4-amino-N-methylpyrimidine-5-carboxamide (0.701 g, isolated yield 85%).

Aufarbeitung

  1. concentrationThe crude was concentrated
  2. dissolutiondissolved in EtOAc
  3. washIt was washed with saturated NaHCO3 solution
  4. customThe solvent was removed
  5. customthe crude was purified by silica gel chromatography (0%˜20% MeOH/DCM)

Quellen und Nachweise

ORD-Eintrag
ord-4fbe223b193d407082a56e5b2ff038b2
Quelldatensatz
uspto-grants-2013_08
Patentnummer
US08501763B2

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