Benzyl Bromide → 3-Benzyl-6-(methylamino)pyrimidin-4(3H)-one

HRID 1260435Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1260435
[CH3:1][NH:2][C:3]1[N:8]=[CH:7][NH:6][C:5](=[O:9])[CH:4]=1.[CH2:10](Br)[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1.C(=O)([O-])[O-].[K+].[K+]>C(O)C>[CH2:10]([N:6]1[C:5](=[O:9])[CH:4]=[C:3]([NH:2][CH3:1])[N:8]=[CH:7]1)[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1

Komponenten

5

Edukt 3

HCID 7498Benzyl BromideHCID 11430Potassium CarbonateHCID 1354814476-(Methylamino)pyrimidin-4-ol2×

Produkt 1

HCID 598230553-Benzyl-6-(methylamino)pyrimidin-4(3H)-oneAusbeute 43,6 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel

Versuchsvorschrift

6-(Methylamino)pyrimidin-4(3H)-one (compound 1B) (3 g, 24 mmol, 1 eq), benzyl bromide (5.7 mL, 48 mmol, 2 eq) and potassium carbonate (6.96 g, 50.4 mmol, 2.1 eq) were stirred in ethanol (30 mL) at RT overnight. The solvent was removed in vacuo and the residue purified by silica chromatography to give 2.25 g of the title compound (43%). 1H NMR (400 MHz, DMSO-d6) δ ppm 2.64 (d, J=4.29 Hz, 3H) 4.92-5.01 (m, 2H) 6.96 (q, J=4.63 Hz, 1H) 7.22-7.30 (m, 3H) 7.30-7.37 (m, 2H) 8.24 (s, 1H). [M+H] calc'd for C12H13N3O, 216. found, 216.

Aufarbeitung

  1. customThe solvent was removed in vacuo
  2. customthe residue purified by silica chromatography

Quellen und Nachweise

ORD-Eintrag
ord-889d6c182b56438692800552ea1649e6
Quelldatensatz
uspto-grants-2013_06
Patentnummer
US08470837B2

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