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2-Amino-4,6-dichloropyrimidine → 6-chloro-N4-(4-{[2-(trifluoromethyl)pyridin-4-yl]oxy}phenyl)pyrimidine-2,4-diamine

HRID 729924
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Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 729924
[NH2:1][C:2]1[N:7]=[C:6](Cl)[CH:5]=[C:4]([Cl:9])[N:3]=1.[F:10][C:11]([F:27])([F:26])[C:12]1[CH:17]=[C:16]([O:18][C:19]2[CH:24]=[CH:23][C:22]([NH2:25])=[CH:21][CH:20]=2)[CH:15]=[CH:14][N:13]=1>O.C(O)(C)C.Cl>[Cl:9][C:4]1[N:3]=[C:2]([NH2:1])[N:7]=[C:6]([NH:25][C:22]2[CH:23]=[CH:24][C:19]([O:18][C:16]3[CH:15]=[CH:14][N:13]=[C:12]([C:11]([F:27])([F:10])[F:26])[CH:17]=3)=[CH:20][CH:21]=2)[CH:5]=1
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

6

Edukt 2

HCID 655222-Amino-4,6-dichloropyrimidineHCID 591345604-{[2-(Trifluoromethyl)pyridin-4-yl]oxy}aniline2×

Produkt 1

HCID 578333536-chloro-N4-(4-{[2-(trifluoromethyl)pyridin-4-yl]oxy}phenyl)pyrimidine-2,4-diamine

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 313Hydrochloric AcidLösungsmittelHCID 962WaterLösungsmittel
HCID 3776
Isopropanol
Lösungsmittel

Reaktionsbedingungen

Temperatur
65 °C

Versuchsvorschrift

A stirred solution containing 2-amino-4,6-dichloropyrimidine (17.74 g, 0.11 mol) and 4-{[2-(trifluoromethyl)pyridin-4-yl]oxy}aniline (Intermediate 2U) in water (400 mL), isopropanol (100 mL) and concentrated hydrochloric acid (5 mL) was heated at 65° C. for 18 h. The reaction was cooled to 0° C. and the yellow-tan solid was collected by suction filtration and washed with water. The filtered product was dissolved in hot N,N-dimethylformamide (90° C.) and triethylamine was slowly added until the solution was slightly basic (pH˜8). The solution was then cooled to rt, added to vigorously stirred ice water (1.2 L), and stirring was continued for 1 h. The tan solids were collected by suction filtration and washed sequentially with water, isopropanol, diethyl ether and finally hexane. The material was dried by air suction to afford a light tan solid, 28.8 g (77%). 1H NMR (DMSO-d6) δ ppm 9.46 (s, 1H), 8.59 (d, 1H, J=5.6 Hz), 7.81 (d, 2H, J=9.0), 7.37 (d, 1H, J=2.4 Hz), 7.17 (d, 2H, J=9.0 Hz), 7.11 (dd, 1H, J=2.6, 5.6 Hz), 6.78 (s, 2H), 6.00 (s, 1H).

Aufarbeitung

  1. temperatureThe reaction was cooled to 0° C.
  2. filtrationthe yellow-tan solid was collected by suction filtration
  3. washwashed with water
  4. dissolutionThe filtered product was dissolved in hot N,N-dimethylformamide (90° C.)
  5. additiontriethylamine was slowly added until the solution
  6. temperatureThe solution was then cooled to rt
  7. additionadded to vigorously stirred ice water (1.2 L)
  8. filtrationThe tan solids were collected by suction filtration
  9. washwashed sequentially with water, isopropanol, diethyl ether and finally hexane
  10. customThe material was dried by air suction
  11. customto afford a light tan solid, 28.8 g (77%)

Quellen und Nachweise

ORD-Eintrag
ord-e12642cf67f341b38bd331d5685ed3a9
Quelldatensatz
uspto-grants-2009_09
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US07582645B2

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