Acetonitrile → 4-(1-Isopropyl-2-methylimidazol-5-yl)-2-[4-(3-morpholinopropylthio)anilino]pyrimidine

HRID 2375298

Reaktionsgleichung

Reaktionsgleichung von HRID 2375298
[CH:1]([N:4]1[C:8]([C:9]2[CH:14]=[CH:13][N:12]=[C:11]([NH:15][C:16]3[CH:21]=[CH:20][C:19]([S:22][CH2:23][CH2:24][CH2:25]O)=[CH:18][CH:17]=3)[N:10]=2)=[CH:7][N:6]=[C:5]1[CH3:27])([CH3:3])[CH3:2].C(#N)C.[CH2:31]([N:33](CC)[CH2:34][CH3:35])[CH3:32].CS(Cl)(=O)=[O:40]>C(Cl)Cl>[CH:1]([N:4]1[C:8]([C:9]2[CH:14]=[CH:13][N:12]=[C:11]([NH:15][C:16]3[CH:17]=[CH:18][C:19]([S:22][CH2:23][CH2:24][CH2:25][N:33]4[CH2:34][CH2:35][O:40][CH2:32][CH2:31]4)=[CH:20][CH:21]=3)[N:10]=2)=[CH:7][N:6]=[C:5]1[CH3:27])([CH3:2])[CH3:3]

Komponenten

6

Edukt 4

HCID 6342AcetonitrileHCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 693131084-(1-Isopropyl-2-methylimidazol-5-yl)-2-[4-(3-hydroxypropylthio)anilino]pyrimidine

Produkt 1

HCID 693106194-(1-Isopropyl-2-methylimidazol-5-yl)-2-[4-(3-morpholinopropylthio)anilino]pyrimidineAusbeute 88 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Reaktionsbedingungen

Temperatur
80 °C

Versuchsvorschrift

4-(1-Isopropyl-2-methylimidazol-5-yl)-2-[4-(3-hydroxypropylthio)anilino]pyrimidine (Method 84; 250 mg, 0.65 mmol) was suspended in DCM (8 ml) and acetonitrile (2 ml) and the stirred at room temperature under nitrogen. Triethylamine (100 μl) was added followed by dropwise addition of methane sulphonyl chloride (50 μl). The mixture was stirred for 2.5 hours and then allowed to stand for 18 hours. The volatiles were removed by evaporation, the residue dissolved in acetonitrile (5 ml), and morpholine (120 μl) and potassium carbonate (50 mg) were added. The mixture was stirred and heated at 80° C. for 3.5 hours and then the volatiles were removed by evaporation. The residue was partitioned between EtOAc (50 ml) and water (20 ml). The aqueous layer was basified to pH 9 with sodium bicarbonate solution. The phases separated and the aqueous layer re-extracted with EtOAc. The extracts were combined, washed with water (10 ml) and brine (10 ml), dried and then evaporated to give the title compound (260 mg, 88%) m/z 453.

Aufarbeitung

  1. waitto stand for 18 hours
  2. customThe volatiles were removed by evaporation
  3. dissolutionthe residue dissolved in acetonitrile (5 ml)
  4. additionmorpholine (120 μl) and potassium carbonate (50 mg) were added
  5. stirringThe mixture was stirred
  6. customthe volatiles were removed by evaporation
  7. customThe residue was partitioned between EtOAc (50 ml) and water (20 ml)
  8. customThe phases separated
  9. extractionthe aqueous layer re-extracted with EtOAc
  10. washwashed with water (10 ml) and brine (10 ml)
  11. customdried
  12. customevaporated

Quellen und Nachweise

ORD-Eintrag
ord-aecfb62c33804ccfa2db9f65477ab6b7
Quelldatensatz
uspto-grants-2008_12
Patentnummer
US07465728B2

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