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

HRID 1660875Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1660875
[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-2fe2fb532afe438baea372da3a480782
Quelldatensatz
uspto-grants-2011_10
Patentnummer
US08030317B2

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