Potassium Carbonate → (+/-)-3-[7-[3-(2-hydroxy-ethyl)-phenylamino]-3-(4-methoxy-phenyl)-4-methyl-2-oxo-3,4-dihydro-2H-pyrimido[4,5-d]pyrimidin-1-yl]-benzonitrile

HRID 1247643Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1247643
[C:1]([C:3]1[CH:4]=[C:5]([N:9]2[C:14]3[N:15]=[C:16]([NH:19][C:20]4[CH:21]=[C:22]([CH2:26][CH2:27][O:28]C(=O)C)[CH:23]=[CH:24][CH:25]=4)[N:17]=[CH:18][C:13]=3[CH:12]([CH3:32])[N:11]([C:33]3[CH:38]=[CH:37][C:36]([O:39][CH3:40])=[CH:35][CH:34]=3)[C:10]2=[O:41])[CH:6]=[CH:7][CH:8]=1)#[N:2].C(=O)([O-])[O-].[K+].[K+]>CO.O>[OH:28][CH2:27][CH2:26][C:22]1[CH:21]=[C:20]([NH:19][C:16]2[N:15]=[C:14]3[N:9]([C:5]4[CH:4]=[C:3]([CH:8]=[CH:7][CH:6]=4)[C:1]#[N:2])[C:10](=[O:41])[N:11]([C:33]4[CH:38]=[CH:37][C:36]([O:39][CH3:40])=[CH:35][CH:34]=4)[CH:12]([CH3:32])[C:13]3=[CH:18][N:17]=2)[CH:25]=[CH:24][CH:23]=1

Komponenten

5

Edukt 2

HCID 11430Potassium CarbonateHCID 10256942(+/-)-Acetic acid 2-{3-[8-(3-cyano-phenyl)-6-(4-methoxy-phenyl)-5-methyl-7-oxo-5,6,7,8-tetrahydro-pyrimido[4,5-d]pyrimidin-2-ylamino]-phenyl}-ethyl ester

Produkt 1

HCID 9870839(+/-)-3-[7-[3-(2-hydroxy-ethyl)-phenylamino]-3-(4-methoxy-phenyl)-4-methyl-2-oxo-3,4-dihydro-2H-pyrimido[4,5-d]pyrimidin-1-yl]-benzonitrile

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 887MethanolLösungsmittelHCID 962WaterLösungsmittel

Versuchsvorschrift

Acetic acid (±)-2-{3-[8-(3-cyano-phenyl)-6-(4-methoxy-phenyl)-5-methyl-7-oxo-5,6,7,8-tetrahydro-pyrimido[4,5-d]pyrimidin-2-ylamino]-phenyl}-ethyl ester (10 g; 1.81 mmol) (from Example 3c supra) was dissolved in a mixture of methanol (17 mL) and water (7 mL) and treated with potassium carbonate (1.00 g; 7.26 mmol) at room temperature for 19 hours. The reaction mixture was partitioned between ethyl acetate and water-brine mixture. The organic phase was washed with brine, dried over anhydrous sodium sulfate, filtered and concentrated. The crude material was purified by flash chromatography (Biotage 40M; ethyl acetate) to give (±)-3-[7-[3-(2-hydroxy-ethyl)-phenylamino]-3-(4-methoxy-phenyl)-4-methyl-2-oxo-3,4-dihydro-2H-pyrimido[4,5-d]pyrimidin-1-yl]-benzonitrile. (Yield 0.67 g; 72.9%). A small amount of additional material bumped over into the solvent trap during concentration. This material was recovered and crystallized from ethyl acetate. (Yield 0.09 g; 9.9%). Melting Point: 195–200° C. HR-MS(ES+) m/z Calculated for C29H26N6O3 ([M+H]+): 507.2139. Found: 507.2145. HR-MS(ES+) m/z Calculated for C29H26N6O3 ([M+Na]+): 529.9158. Found: 529.1963.

Aufarbeitung

  1. customThe reaction mixture was partitioned between ethyl acetate and water-brine mixture
  2. washThe organic phase was washed with brine
  3. dry with materialdried over anhydrous sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe crude material was purified by flash chromatography (Biotage 40M; ethyl acetate)

Quellen und Nachweise

ORD-Eintrag
ord-7ba85dcfc319497b8a49e156595312e8
Quelldatensatz
uspto-grants-2006_10
Patentnummer
US07129351B2

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