Trifluoroacetic acid → N4-(3,4-dichlorophenyl)pyrido[3,4-d]pyrimidine-4,6-diamine

HRID 511800Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 511800
[Cl:1][C:2]1[CH:3]=[C:4]([NH:9][C:10]2[C:11]3[CH:19]=[C:18]([NH:20]CC4C=CC(OC)=CC=4)[N:17]=[CH:16][C:12]=3[N:13]=[CH:14][N:15]=2)[CH:5]=[CH:6][C:7]=1[Cl:8].FC(F)(F)C(O)=O.C1(OC)C=CC=CC=1>C(Cl)Cl>[Cl:1][C:2]1[CH:3]=[C:4]([NH:9][C:10]2[C:11]3[CH:19]=[C:18]([NH2:20])[N:17]=[CH:16][C:12]=3[N:13]=[CH:14][N:15]=2)[CH:5]=[CH:6][C:7]=1[Cl:8]

Komponenten

5

Edukt 3

HCID 6422Trifluoroacetic acidHCID 7519AnisoleHCID 86668934N4-(3,4-dichlorophenyl)-N6-(4-methoxybenzyl)pyrido[3,4-d]pyrimidine-4,6-diamine

Produkt 1

HCID 86668935N4-(3,4-dichlorophenyl)pyrido[3,4-d]pyrimidine-4,6-diamineAusbeute 98,1 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

To a stirred heterogeneous mixture of compound 213 (2.50 g, 5.86 mmol) and DCM (60 ml) was added trifluoroacetic acid (4.49 ml, 58.6 mmol), followed by anisole (1.28 mL, 11.7 mmol), and the mixture was stirred further at room temperature for 43 h. It was poured into petroleum ether (600 mL) and stirred at room temperature for ca. 20 min. Petroleum ether layer was decanted and discarded. The process was repeated with more petroleum ether (300 mL). To the solid left behind was added 5M NH3 (80 mL) at 0° C. and stirred at room temperature for 15 min. The solid was collected and washed successively with water (6×10 mL), petroleum ether-ethyl acetate=3:1 (3×20 mL), and dried to give N4-(3,4-dichlorophenyl)pyrido[3,4-d]pyrimidine-4,6-diamine (222) (1.76 g, 98%), mp 277-280° C.; 1H NMR δ [(CD3)2SO] 9.83 (s, 1H), 8.73 (s, 1H), 8.42 (s, 1H), 8.34 (d, J=2.5 Hz, 1H), 7.92 (dd, J=8.8, 2.5 Hz, 1H), 7.63 (d, J=8.8 Hz, 1H), 7.14 (s, 1H), 6.30 (s, 2H). Anal. Calcd for C13H9Cl2N5.0.5H2O: C, 49.54; H, 3.20; N, 22.22. Found C, 49.70; H, 3.08; N, 22.28.

Aufarbeitung

  1. stirringstirred at room temperature for ca. 20 min
  2. customPetroleum ether layer was decanted
  3. waitTo the solid left behind
  4. additionwas added 5M NH3 (80 mL) at 0° C.
  5. stirringstirred at room temperature for 15 min
  6. customThe solid was collected
  7. washwashed successively with water (6×10 mL), petroleum ether-ethyl acetate=3:1 (3×20 mL)
  8. customdried

Quellen und Nachweise

ORD-Eintrag
ord-8b2c87909806431b8af58f7f219b0bf0
Quelldatensatz
uspto-grants-2015_08
Patentnummer
US09101632B2

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