Phosphorus oxychloride → 5-Chloro-2-(morpholin-4-ylmethyl)-7-[4-(trifluoromethyl)phenyl][1,2,4]triazolo[1,5-c]pyrimidine

HRID 2171552Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2171552
[N:1]1([CH2:7][C:8]2[N:16]=[C:15]3[N:10]([C:11](O)=[N:12][C:13]([C:17]4[CH:22]=[CH:21][C:20]([C:23]([F:26])([F:25])[F:24])=[CH:19][CH:18]=4)=[CH:14]3)[N:9]=2)[CH2:6][CH2:5][O:4][CH2:3][CH2:2]1.C(=O)(O)[O-].[Na+].P(Cl)(Cl)([Cl:35])=O>[Cl-].C([N+](CC)(CC)CC)C1C=CC=CC=1>[Cl:35][C:11]1[N:10]2[N:9]=[C:8]([CH2:7][N:1]3[CH2:6][CH2:5][O:4][CH2:3][CH2:2]3)[N:16]=[C:15]2[CH:14]=[C:13]([C:17]2[CH:22]=[CH:21][C:20]([C:23]([F:26])([F:25])[F:24])=[CH:19][CH:18]=2)[N:12]=1

Komponenten

5

Edukt 3

HCID 24813Phosphorus oxychlorideHCID 516892Sodium BicarbonateHCID 178517471HCID 178517471, Verbindung

Produkt 1

HCID 593131385-Chloro-2-(morpholin-4-ylmethyl)-7-[4-(trifluoromethyl)phenyl][1,2,4]triazolo[1,5-c]pyrimidine

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 66133Benzyl triethylammonium chlorideKatalysator

Reaktionsbedingungen

Temperatur
120 °C

Versuchsvorschrift

850 mg (2.2 mmol) of 2-(morpholin-4-ylmethyl)-7-[4-(trifluoromethyl)phenyl][1,2,4]triazolo-[1,5-c]pyrimidin-5-ol (Example 135A) are introduced into phosphoryl chloride (20 ml), 1.98 g (8.7 mmol) of benzyltriethylammonium chloride are added, and the reaction mixture is stirred at 120° C. for 2 h. The reaction mixture is slowly poured, while stirring vigorously, into ice-water, and solid sodium bicarbonate is added until a pH of 8 is reached. The reaction mixture is extracted with ethyl acetate (150 ml), and the organic phase is separated off, dried (magnesium sulphate) and concentrated. The residue is chromatographed on silica gel (mobile phase dichloromethane/ethanol 100:1 to 20:1). 650 mg (75% of theory) of the product are obtained as a solid.

Aufarbeitung

  1. additionare added
  2. additionThe reaction mixture is slowly poured
  3. additionis added until a pH of 8
  4. extractionThe reaction mixture is extracted with ethyl acetate (150 ml)
  5. customthe organic phase is separated off
  6. dry with materialdried (magnesium sulphate)
  7. concentrationconcentrated
  8. customThe residue is chromatographed on silica gel (mobile phase dichloromethane/ethanol 100:1 to 20:1)
  9. custom650 mg (75% of theory) of the product are obtained as a solid

Quellen und Nachweise

ORD-Eintrag
ord-f93aea2ae6ad4779bc1961212b0cd302
Quelldatensatz
uspto-grants-2015_06
Patentnummer
US09051323B2

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