Hydrochloric Acid → N-benzylpyrido[3,2-d]pyrimidin-4-amine

HRID 1059548Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1059548
Cl[C:2]1[C:3]2[N:11]=[CH:10][CH:9]=[CH:8][C:4]=2[N:5]=[CH:6][N:7]=1.[CH2:12]([NH2:19])[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.Cl>CC(O)C>[CH2:12]([NH:19][C:2]1[C:3]2[N:11]=[CH:10][CH:9]=[CH:8][C:4]=2[N:5]=[CH:6][N:7]=1)[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1

Komponenten

5

Edukt 3

HCID 313Hydrochloric AcidHCID 7504BenzylamineHCID 131016394-Chloropyrido(3,2-d)pyrimidine

Produkt 1

HCID 5328272N-benzylpyrido[3,2-d]pyrimidin-4-amine

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 3776IsopropanolLösungsmittel

Reaktionsbedingungen

Temperatur
50 °C

Versuchsvorschrift

A solution of freshly prepared 4-chloropyrido[3,2-d]pyrimidine (0.10 g, 0.60 mmol) (prepared as described in the previous experimental) and benzylamine (0.13 mL, 1.20 mmol) in propan-2-ol (15 mL) containing a trace of conc. HCl is warmed at 50° C. for 30 min, and then concentrated to dryness. The residue is partitioned between water and EtOAc, and the organic layer worked up and chromatographed on silica gel. EtOAc elutes foreruns, while MeOH/EtOAc (1:9) elutes 4-(benzylamino)pyrido[3,2-d]pyrimidine (0.11 g, 77%). 1H NMR (CDCl3) δ 8.67 (1H, s), 6.50 (1H, dd, J=4,3, 1.5 Hz), 8.10 (1H, dd, J=8.5, 1.5 Hz), 7.63 (1H, dd, J=8.8, 4,3 Hz), 7.55 (1H, brs), 7.41-7.29 (5H, m), 4.86 (2H, d, J=5.9 Hz).

Aufarbeitung

  1. concentrationconcentrated to dryness
  2. customThe residue is partitioned between water and EtOAc
  3. customchromatographed on silica gel

Quellen und Nachweise

ORD-Eintrag
ord-31aa03fea9434c82bf047096e6f1a229
Quelldatensatz
uspto-grants-2003_02
Patentnummer
US06521620B1

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