Water → 7-amino-4-([R]-1-phenylethylamino)pyrido[4,3-d]pyrimidine

HRID 1281951Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1281951
[C:1]1([C@H:7]([NH2:9])[CH3:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[NH2:10][C:11]1[N:20]=[CH:19][C:18]2[C:17](SC)=[N:16][CH:15]=[N:14][C:13]=2[CH:12]=1.O>C(Cl)(Cl)Cl>[NH2:10][C:11]1[N:20]=[CH:19][C:18]2[C:17]([NH:9][C@@H:7]([C:1]3[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=3)[CH3:8])=[N:16][CH:15]=[N:14][C:13]=2[CH:12]=1

Komponenten

5

Edukt 3

HCID 962WaterHCID 6431891-Phenethylamine, (+)-HCID 104425627-Amino-4-methylthiopyrido[4,3-d]pyrimidine

Produkt 1

HCID 539624137-amino-4-([R]-1-phenylethylamino)pyrido[4,3-d]pyrimidineAusbeute 11 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6212ChloroformLösungsmittel

Reaktionsbedingungen

Temperatur
180 °C

Versuchsvorschrift

A mixture of [R]-1-phenylethylamine (0.072 mL, 0.55 mmol) and 7-amino-4-methylthiopyrido[4,3-d]pyrimidine (97 mg, 0.5 mmol) (described in a previous experimental) is heated at 180° C. under N2 for 1.5 hr. The reaction is then cooled to room temperature producing a precipitate. The mixture is added to water and CHCl3, sonicated and filtered. The phases are separated and the aqueous phase is extracted with CHCl3. The combined extracts are washed with water, saturated brine and dried (MgSO4). The solvent is removed under reduced pressure and the residue purified by using preparative tlc (5% MeOH/CHCl3) and recrystallization from CHCl3 to give 7-amino-4-([R]-1-phenylethylamino)pyrido[4,3-d]pyrimidine (14.5 mg, 11%), mp 231.8-232.1° C. 1H NMR (DMSO) δ 9.23(1H, s), 8.50 (1H, d, J=8.0 Hz), 8.19 (1H, s), 7.41 (2H, d, J=7.0 Hz), 7.31 (2H, t, J=8.0 Hz, 7.21 (1H, tt, J=7.4, 1.2 Hz), 6.45 (2H, s), 6.33 (1H, s), 5.56 (1H, p, J=7.2 Hz), 1.55 (3H, d, J=7.0 Hz).

Aufarbeitung

  1. temperatureThe reaction is then cooled to room temperature
  2. customproducing a precipitate
  3. customsonicated
  4. filtrationfiltered
  5. customThe phases are separated
  6. extractionthe aqueous phase is extracted with CHCl3
  7. washThe combined extracts are washed with water, saturated brine
  8. dry with materialdried (MgSO4)
  9. customThe solvent is removed under reduced pressure
  10. customthe residue purified
  11. customtlc (5% MeOH/CHCl3) and recrystallization from CHCl3

Quellen und Nachweise

ORD-Eintrag
ord-424da2586ede4c9fba3e064781554f16
Quelldatensatz
uspto-grants-2002_09
Patentnummer
US06455534B2

Notizen zur Reaktion

Wird geladen…