Hydrochloric Acid → N4-benzyl-N2-(4-(oxazol-5-yl)phenyl)-5,6,7,8-tetrahydropyrido[4,3-d]pyrimidine-2,4-diamine

HRID 1930543Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1930543
Cl.[CH2:2]([NH:9][C:10]1[C:11]2[CH2:31][N:30](C(OC(C)(C)C)=O)[CH2:29][CH2:28][C:12]=2[N:13]=[C:14]([NH:16][C:17]2[CH:22]=[CH:21][C:20]([C:23]3[O:27][CH:26]=[N:25][CH:24]=3)=[CH:19][CH:18]=2)[N:15]=1)[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1>CO>[CH2:2]([NH:9][C:10]1[C:11]2[CH2:31][NH:30][CH2:29][CH2:28][C:12]=2[N:13]=[C:14]([NH:16][C:17]2[CH:18]=[CH:19][C:20]([C:23]3[O:27][CH:26]=[N:25][CH:24]=3)=[CH:21][CH:22]=2)[N:15]=1)[C:3]1[CH:4]=[CH:5][CH:6]=[CH:7][CH:8]=1

Komponenten

4

Edukt 2

HCID 313Hydrochloric AcidHCID 59333703tert-butyl 4-(benzylamino)-2-(4-(oxazol-5-yl)phenylamino)-7,8-dihydropyrido[4,3-d]pyrimidine-6(5H)-carboxylate

Produkt 1

HCID 46200198N4-benzyl-N2-(4-(oxazol-5-yl)phenyl)-5,6,7,8-tetrahydropyrido[4,3-d]pyrimidine-2,4-diamineAusbeute 75,3 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel

Reaktionsbedingungen

Temperatur
76 °C

Versuchsvorschrift

Hydrochloric acid (2M aq, 2 ml) was added to a solution of tert-butyl 4-(benzylamino)-2-(4-(oxazol-5-yl)phenylamino)-7,8-dihydropyrido[4,3-d]pyrimidine-6(5H)-carboxylate (0.15 g, 0.30 mmol, Example 6a) in MeOH (4 mL). The reaction was heated in an open reaction vessel to 76° C. for 1 h and the product precipitated out from the solution as it was cooled. The crude product was filtered off and washed with water. The crude salt was dissolved in water and precipitated when saturated NaHCO3 was added. The product was filtered off and purified by preparative HPLC to give N4-benzyl-N2-(4-(oxazol-5-yl)phenyl)-5,6,7,8-tetrahydropyrido[4,3-d]pyrimidine-2,4-diamine (0.090 g, 75%). MS (ESI+)/(ESI−) m/z 399/397

Aufarbeitung

  1. customthe product precipitated out from the solution as it
  2. temperaturewas cooled
  3. filtrationThe crude product was filtered off
  4. washwashed with water
  5. dissolutionThe crude salt was dissolved in water
  6. customprecipitated when saturated NaHCO3
  7. additionwas added
  8. filtrationThe product was filtered off
  9. custompurified by preparative HPLC

Quellen und Nachweise

ORD-Eintrag
ord-a3a9807cd56e4028b7fa26bc5d2c2e8d
Quelldatensatz
uspto-grants-2012_05
Patentnummer
US08188101B2

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