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Ammonium Chloride → N2-(2-chloro-4-(2H-tetrazol-5-yl)phenyl)-N4-methyl-5-(trifluoromethyl)pyrimidine-2,4-diamine

HRID 1630335
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1630335
[Cl:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][C:9]=1[NH:10][C:11]1[N:16]=[C:15]([NH:17][CH3:18])[C:14]([C:19]([F:22])([F:21])[F:20])=[CH:13][N:12]=1)[C:5]#[N:6].[N-:23]=[N+:24]=[N-:25].[Na+].[Cl-].[NH4+]>CN(C=O)C>[Cl:1][C:2]1[CH:3]=[C:4]([C:5]2[N:23]=[N:24][NH:25][N:6]=2)[CH:7]=[CH:8][C:9]=1[NH:10][C:11]1[N:16]=[C:15]([NH:17][CH3:18])[C:14]([C:19]([F:20])([F:21])[F:22])=[CH:13][N:12]=1
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

5

Edukt 3

HCID 25517Ammonium ChlorideHCID 33557Sodium AzideHCID 715133123-Chloro-4-(4-(methylamino)-5-(trifluoromethyl)pyrimidin-2-ylamino)benzonitrile

Produkt 1

HCID 71513313N2-(2-chloro-4-(2H-tetrazol-5-yl)phenyl)-N4-methyl-5-(trifluoromethyl)pyrimidine-2,4-diamineAusbeute 85 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228
Dimethylformamide
Lösungsmittel

Reaktionsbedingungen

Temperatur
125 °C

Versuchsvorschrift

To a solution of 3-chloro-4-(4-(methylamino)-5-(trifluoromethyl)pyrimidin-2-ylamino)benzonitrile (135 mg, 6.41 mmol) in DMF (2 mL) was added sodium azide (80 mg, 1.24 mmol) and ammonium chloride (66 mg, 1.24 mmol). The mixture was heated at 125° C. for 18 h. The mixture was cooled, filtered and the solid washed with ethyl acetate. The filtrated was concentrated under reduced pressure and the crude residue was diluted with water (5 mL) and diethyl ether (5 mL). A precipitate formed which was filtered and washed with further portions of water and diethyl ether. The solid was co-evaporated with dichloromethane and methanol and then dried in a vacuum oven to yield N2-(2-chloro-4-(2H-tetrazol-5-yl)phenyl)-N4-methyl-5-(trifluoromethyl)pyrimidine-2,4-diamine (130 mg, 85%). LCMS (ESCI_Formic_MeCN): [MH+]=371 at 3.11 min. 1H NMR (400 MHz, DMSO): δ 8.94 (s, 1H); 8.26-8.19 (m, 2H); 8.14 (d, J=2.0, 1H); 8.03-7.96 (m, 1H); 7.30-7.22 (m, 1H); 2.89 (t, J=4.4, 3H).

Aufarbeitung

  1. temperatureThe mixture was cooled
  2. filtrationfiltered
  3. washthe solid washed with ethyl acetate
  4. concentrationThe filtrated was concentrated under reduced pressure
  5. additionthe crude residue was diluted with water (5 mL) and diethyl ether (5 mL)
  6. customA precipitate formed which
  7. filtrationwas filtered
  8. washwashed with further portions of water and diethyl ether
  9. customdried in a vacuum oven

Quellen und Nachweise

ORD-Eintrag
ord-4d72974d461d48748cf9e0457109dcc8
Quelldatensatz
uspto-grants-2014_07
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08791130B2

Notizen zur Reaktion

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