Sodium Carbonate → Benzenemethanol, 4-((2-amino-6-(5-chloro-2-ethoxyphenyl)-4-pyrimidinyl)amino)-

HRID 28564

Reaktionsgleichung

Reaktionsgleichung von HRID 28564
[NH2:1][C:2]1[N:7]=[C:6]([NH:8][C:9]2[CH:14]=[CH:13][C:12]([CH2:15][OH:16])=[CH:11][CH:10]=2)[CH:5]=[C:4](Cl)[N:3]=1.[Cl:18][C:19]1[CH:20]=[CH:21][C:22]([O:28][CH2:29][CH3:30])=[C:23](B(O)O)[CH:24]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C(=O)([O-])[O-].[Na+].[Na+]>O.C([O-])(=O)C.[Pd+2].C([O-])(=O)C.C(COC)OC>[NH2:1][C:2]1[N:7]=[C:6]([NH:8][C:9]2[CH:14]=[CH:13][C:12]([CH2:15][OH:16])=[CH:11][CH:10]=2)[CH:5]=[C:4]([C:21]2[CH:20]=[C:19]([Cl:18])[CH:24]=[CH:23][C:22]=2[O:28][CH2:29][CH3:30])[N:3]=1

Komponenten

8

Edukt 4

HCID 10340Sodium CarbonateHCID 11776TriphenylphosphineHCID 37008365-Chloro-2-ethoxyphenylboronic acidHCID 86004324[4-(2-Amino-6-chloro-pyrimidin-4-yl-amino)-phenyl]-methanol

Produkt 1

HCID 10406874Benzenemethanol, 4-((2-amino-6-(5-chloro-2-ethoxyphenyl)-4-pyrimidinyl)amino)-Ausbeute 62 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 167845palladium(II) acetateKatalysatorHCID 962WaterLösungsmittelHCID 80711,2-DimethoxyethaneLösungsmittel

Reaktionsbedingungen

Temperatur
100 °C

Versuchsvorschrift

To a mixture of [4-(2-amino-6-chloro-pyrimidin-4-yl-amino)-phenyl]-methanol (6.0 g, 24 mmol), 5-chloro-2-ethoxy-phenyl boronic acid (7.7 g, 38.4 mmol), palladium (II) acetate (0.54 g, 2.4 mmol) and triphenylphosphine (1.26 g, 4.8 mmol) was added a solution of sodium carbonate (12.7 g, 120 mmol) in water (80 ml) followed by glyme (300 ml). The mixture was stirred under an argon atmosphere at 95-105° C. for 18 hours. Filtration and concentration of the filtrate yielded a residue which was purified by flash chromatography on silica gel eluting with ethyl acetate-hexane (1:3) to provide the title compound (5.5 g, 62% yield) as a white powder. 1H NMR (DMSO-d6) δ 1.38 (t, 3H, J=6.9 Hz, CH3), 4.13 (q, 2H, J=6.9 Hz, CH2), 4.45 (d, 2H, J=5.7 Hz, CH2), 5.07 (t, 1H, J=5.7 Hz, OH), 6.26 (s, 2H, NH2), 6.77 (s, 1H, Ar), 7.14 (d, 1H, J-8.9 Hz, Ar), 7.24 (d, 2H, J=8.4 Hz, Ar), 7.41 (dd, 1H, J=8.8, 2.8 Hz, Ar), 7.64 (d, 2H, J=8.3 Hz, Ar), 7.93 (d, 1H, J=2.8 Hz, Ar), 9.12 (s, 1H, NH).

Aufarbeitung

  1. filtrationFiltration and concentration of the filtrate
  2. customyielded a residue which
  3. customwas purified by flash chromatography on silica gel eluting with ethyl acetate-hexane (1:3)

Quellen und Nachweise

ORD-Eintrag
ord-51f35f4286bf40dfb7470606352fef74
Quelldatensatz
uspto-grants-2008_09
Patentnummer
US07419984B2

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