HCID 67328269, Verbindung → HCID 53373261, Verbindung

HRID 1846177Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1846177
C([O:8][C:9]1[C:10]([CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][O:27]COC)=[N:11][C:12]([NH2:16])=[N:13][C:14]=1[CH3:15])C1C=CC=CC=1>CO.Cl.[OH-].[OH-].[Pd+2]>[NH2:16][C:12]1[N:11]=[C:10]([CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][OH:27])[C:9]([OH:8])=[C:14]([CH3:15])[N:13]=1

Komponenten

5

Edukt 1

HCID 67328269HCID 67328269, Verbindung

Produkt 1

HCID 53373261HCID 53373261, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 313Hydrochloric AcidKatalysatorHCID 9942167Palladium hydroxideKatalysatorHCID 887MethanolLösungsmittel

Versuchsvorschrift

To a stirred solution containing 133 mg (0.48 mmol) of 5-(benzyloxy)-4-(10-(methoxymethoxy)decyl)-6-methylpyrimidin-2-amine in 10 mL of methanol were added two drops of concentrated HCl and the mixture was stirred at reflux for 16 h. To the mixture were added 10 mg of 20% palladium hydroxide on carbon (Degussa type E101 NE/N). The reaction mixture was stirred at 23° C. under hydrogen atmosphere for 15 min. The reaction mixture was filtered through celite and the filtrated was concentrated under diminished pressure. The residue was purified by chromatography on a silica gel column (13×3 cm). Elution with 17:3 dichloromethane-methanol afforded the expected product as white solid: yield 68 mg (69%); mp: 103-104° C.; silica gel TLC Rf 0.20 (17:3 dichloromethane-methanol); 1H NMR (methanol-d4) δ 1.29-1.35 (m, 12H), 1.50 (quint, 2H, J=6.8 Hz), 1.64 (quint, 2H, J=7.6 Hz), 2.37 (s, 3H), 2.71 (dd, 2H, J=7.6, 7.6 Hz) and 3.51 (t, 2H, J=6.4); 13C NMR (methanol-d4) δ 16.42, 25.50, 27.07, 29.00, 29.02, 29.08, 29.13, 29.25, 30.72, 32.22, 61.56, 138.97, 153.46, 157.60 and 160.84; mass spectrum (APCI+), m/z 282.2170 (M+H) (C15H28N3O2 requires 282.2182).

Aufarbeitung

  1. temperatureat reflux for 16 h
  2. stirringThe reaction mixture was stirred at 23° C. under hydrogen atmosphere for 15 min
  3. filtrationThe reaction mixture was filtered through celite
  4. concentrationthe filtrated was concentrated under diminished pressure
  5. customThe residue was purified by chromatography on a silica gel column (13×3 cm)
  6. washElution with 17:3 dichloromethane-methanol

Quellen und Nachweise

ORD-Eintrag
ord-22e1a813c20d4290a8bb8a11dfcca3a0
Quelldatensatz
uspto-grants-2015_02
Patentnummer
US08952025B2

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