Triethylamine → HCID 178430504, Verbindung

HRID 1678077Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1678077
[Cl:1][CH2:2][CH2:3][CH2:4][CH2:5][N:6]1[CH:11]=[C:10]([CH3:12])[C:9]([OH:13])=[N:8][C:7]1=[O:14].[C:15]([C:19]1[N:24]=[C:23]([N:25]2[CH2:30][CH2:29][NH:28][CH2:27][CH2:26]2)[CH:22]=[C:21]([C:31]([F:34])([F:33])[F:32])[N:20]=1)([CH3:18])([CH3:17])[CH3:16].CCN(CC)CC.C(OCC)(=O)C>CN(C)C=O>[Cl-:1].[C:15]([C:19]1[N:24]=[C:23]([N:25]2[CH2:26][CH2:27][NH+:28]([CH2:2][CH2:3][CH2:4][CH2:5][N:6]3[CH:11]=[C:10]([CH3:12])[C:9]([OH:13])=[N:8][C:7]3=[O:14])[CH2:29][CH2:30]2)[CH:22]=[C:21]([C:31]([F:32])([F:33])[F:34])[N:20]=1)([CH3:18])([CH3:16])[CH3:17]

Komponenten

6

Edukt 4

HCID 8471TriethylamineHCID 8857Ethyl AcetateHCID 183996102-(tert-Butyl)-4-(piperazin-1-yl)-6-(trifluoromethyl)pyrimidineHCID 593375871-(4-chlorobutyl)-5-methylpyrimidine-2,4(1H,3H)-dione

Produkt 1

HCID 178430504HCID 178430504, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

1.5 g (7.0 mmol) of 1-(4-chlorobutyl)-4-hydroxy-5-methylpyrimidin-2(1H)-one from Example 5.2.1, 2.0 g (7.0 mmol) of 2-tert-butyl-4-piperazin-1-yl-6-(trifluoromethyl)pyrimidine (DE 197 35 410) and 1.4 g (14.0 mmol) of NEt3 in 100 ml of N,N-dimethylformamide (DMF) were stirred at 110° C. for 24 hours. Then ethyl acetate was added, and the mixture was washed twice with water. The combined organic phases were dried over Na2SO4, filtered to remove the desiccant and concentrated in vacuo. The oily residue was purified by chromatography on silica gel (eluent: dichloromethane:methanol 95:5 v/v), and stirred with pentane and filtered off with suction. The solid was taken up in a little methylene chloride, and a solution of HCl in diethyl ether was added, whereupon the required product precipitated as hydrochloride. The hydrochloride was filtered off with suction and washed with diethyl ether, and the title compound was dried in vacuo at 40° C. Yield: 1.1 g.

Aufarbeitung

  1. washthe mixture was washed twice with water
  2. dry with materialThe combined organic phases were dried over Na2SO4
  3. filtrationfiltered
  4. customto remove the desiccant and
  5. concentrationconcentrated in vacuo
  6. customThe oily residue was purified by chromatography on silica gel (eluent: dichloromethane:methanol 95:5 v/v)
  7. filtrationfiltered off with suction
  8. additiona solution of HCl in diethyl ether was added, whereupon the required product
  9. customprecipitated as hydrochloride
  10. filtrationThe hydrochloride was filtered off with suction
  11. washwashed with diethyl ether
  12. dry with materialthe title compound was dried in vacuo at 40° C

Quellen und Nachweise

ORD-Eintrag
ord-280a3e5d8793426ebb96301d40503acd
Quelldatensatz
uspto-grants-2011_08
Patentnummer
US08008488B2

Notizen zur Reaktion

Wird geladen…