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Water → N4-(3,4-dibromophenyl)-N6-(4-methoxybenzyl)pyrido[3,4-d]pyrimidine-4,6-diamine

HRID 511808
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 511808
[Br:1][C:2]1[CH:3]=[C:4]([NH:9][C:10]2[C:11]3[CH:19]=[C:18](F)[N:17]=[CH:16][C:12]=3[N:13]=[CH:14][N:15]=2)[CH:5]=[CH:6][C:7]=1[Br:8].[CH3:21][O:22][C:23]1[CH:30]=[CH:29][C:26]([CH2:27][NH2:28])=[CH:25][CH:24]=1.O>CS(C)=O>[Br:1][C:2]1[CH:3]=[C:4]([NH:9][C:10]2[C:11]3[CH:19]=[C:18]([NH:28][CH2:27][C:26]4[CH:29]=[CH:30][C:23]([O:22][CH3:21])=[CH:24][CH:25]=4)[N:17]=[CH:16][C:12]=3[N:13]=[CH:14][N:15]=2)[CH:5]=[CH:6][C:7]=1[Br:8]
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

5

Edukt 3

HCID 962Water2×HCID 754524-MethoxybenzylamineHCID 68158675N-(3,4-dibromophenyl)-6-fluoropyrido[3,4-d]pyrimidin-4-amine

Produkt 1

HCID 86668940N4-(3,4-dibromophenyl)-N6-(4-methoxybenzyl)pyrido[3,4-d]pyrimidine-4,6-diamineAusbeute 95 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 679Dimethyl Sulfoxide
Lösungsmittel

Reaktionsbedingungen

Temperatur
70 °C

Versuchsvorschrift

A mixture of compound 207 (3.40 g, 8.54 mmol) and 4-methoxybenzylamine (11.2 mL, 85.4 mmol) in dry DMSO (22 mL) was stirred under a nitrogen atmosphere at 70° C. (bath temperature) for 138 h. The mixture was then cooled and poured into water (400 mL). Petroleum ether (400 mL) was added and stirred at room temperature for 30 min. The layers were allowed to separate and the petroleum ether layer was decanted. This procedure was repeated with more petroleum ether (400 mL). It was filtered and washed solid with water (3×30 mL). The sticky yellow/orange solid was stirred with acetone (100 mL) at room temperature for ca. 30 min. to give a fine orange precipitate. Water (200 mL) was added and stirred further at room temperature for 2 h. The solid was collected by suction-filtration, washed with water/acetone (2:1) (5×30 mL), and dried in vacuum over silica-gel/KOH to give pure N4-(3,4-dibromophenyl)-N6-(4-methoxybenzyl)pyrido[3,4-d]pyrimidine-4,6-diamine (216) (4.16 g, 95%) as a greenish yellow solid, mp 166-169° C.; 1H NMR δ [(CD3)2SO] 9.72 (s, 1H), 8.77 (s, 1H, 8.42 (s, 1H), 8.40 (br s, 1H), 7.89 (br d, J=7.7 Hz, 1H), 7.76 (d, J=8.7, Hz, 1H), 7.40-7.25 (m, 3H), 7.17 (s, 1H), 6.88 (br d, J=8.3 Hz, 2H), 4.49 (d, J=5.9 Hz, 2H), 3.71 (s, 3H). Anal. Calcd for C21H17Br2N5O.0.25hexane: C, 50.35; H, 3.85; N, 13.05%. Found C, 50.56; H, 3.54; N, 12.87%.

Aufarbeitung

  1. temperatureThe mixture was then cooled
  2. stirringstirred at room temperature for 30 min
  3. customto separate
  4. customthe petroleum ether layer was decanted
  5. filtrationIt was filtered
  6. washwashed solid with water (3×30 mL)
  7. stirringThe sticky yellow/orange solid was stirred with acetone (100 mL) at room temperature for ca. 30 min.
  8. customto give a fine orange precipitate
  9. stirringstirred further at room temperature for 2 h
  10. filtrationThe solid was collected by suction-filtration
  11. washwashed with water/acetone (2:1) (5×30 mL)
  12. dry with materialdried in vacuum over silica-gel/KOH

Quellen und Nachweise

ORD-Eintrag
ord-c5ff095c2f7144868d6863f9b790f230
Quelldatensatz
uspto-grants-2015_08
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US09101632B2

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