Hydrochloric Acid → 2-((2-(4-(Oxazol-5-yl)phenylamino)-5,6,7,8-tetrahydropyrido[4,3-d]pyrimidin-4-yl)(phenyl)amino)ethanol

HRID 1930533Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1930533
Cl.[OH:2][CH2:3][CH2:4][N:5]([C:35]1[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=1)[C:6]1[C:7]2[CH2:27][N:26](C(OC(C)(C)C)=O)[CH2:25][CH2:24][C:8]=2[N:9]=[C:10]([NH:12][C:13]2[CH:18]=[CH:17][C:16]([C:19]3[O:23][CH:22]=[N:21][CH:20]=3)=[CH:15][CH:14]=2)[N:11]=1.O>CO>[O:23]1[C:19]([C:16]2[CH:17]=[CH:18][C:13]([NH:12][C:10]3[N:11]=[C:6]([N:5]([C:35]4[CH:36]=[CH:37][CH:38]=[CH:39][CH:40]=4)[CH2:4][CH2:3][OH:2])[C:7]4[CH2:27][NH:26][CH2:25][CH2:24][C:8]=4[N:9]=3)=[CH:14][CH:15]=2)=[CH:20][N:21]=[CH:22]1

Komponenten

5

Edukt 3

HCID 313Hydrochloric AcidHCID 962WaterHCID 59333719tert-butyl 4-((2-hydroxyethyl)(phenyl)amino)-2-(4-(oxazol-5-yl)phenylamino)-7,8-dihydropyrido[4,3-d]pyrimidine-6(5H)-carboxylate

Produkt 1

HCID 462000502-((2-(4-(Oxazol-5-yl)phenylamino)-5,6,7,8-tetrahydropyrido[4,3-d]pyrimidin-4-yl)(phenyl)amino)ethanolAusbeute 60 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel

Reaktionsbedingungen

Temperatur
70 °C

Versuchsvorschrift

Hydrochloric acid (2 M, 2 ml) was added to a solution of tert-butyl 4-((2-hydroxyethyl)(phenyl)amino)-2-(4-(oxazol-5-yl)phenylamino)-7,8-dihydropyrido[4,3-d]pyrimidine-6(5H)-carboxylate (150 mg, 0.28 mmol, Example 1a) in methanol (4 mL). Water (2 mL) was added and the solution was stirred at 70° C. for 30 min. The residual solvent was evaporated under reduced pressure and the crude product dissolved in DMSO. Purification by preparative HPLC afforded 2-((2-(4-(oxazol-5-yl)phenylamino)-5,6,7,8-tetrahydropyrido[4,3-d]pyrimidin-4-yl)(phenyl)amino)ethanol (72 mg, 54.8%). MS (ESI+)/(ESI−) m/z 429/427

Aufarbeitung

  1. customThe residual solvent was evaporated under reduced pressure
  2. dissolutionthe crude product dissolved in DMSO
  3. customPurification by preparative HPLC

Quellen und Nachweise

ORD-Eintrag
ord-f81db7da34174f9c95a53ce6b562786d
Quelldatensatz
uspto-grants-2012_05
Patentnummer
US08188101B2

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