Triethylamine → 1-[(alpha-Cyclopropyl-alpha-hydroxy-o-tolyl)sulfamoyl]-3-(4,6-dimethoxy-2-pyrimidinyl)urea

HRID 128532

Reaktionsgleichung

Reaktionsgleichung von HRID 128532
Cl[S:2]([N:5]=[C:6]=[O:7])(=[O:4])=[O:3].[NH2:8][C:9]1[N:14]=[C:13]([O:15][CH3:16])[CH:12]=[C:11]([O:17][CH3:18])[N:10]=1.[NH2:19][C:20]1[CH:30]=[CH:29][CH:28]=[CH:27][C:21]=1[CH:22]([OH:26])[CH:23]1[CH2:25][CH2:24]1.C(N(CC)CC)C>C(Cl)Cl.C(OCC)(=O)C>[CH:23]1([CH:22]([OH:26])[C:21]2[CH:27]=[CH:28][CH:29]=[CH:30][C:20]=2[NH:19][S:2]([NH:5][C:6]([NH:8][C:9]2[N:10]=[C:11]([O:17][CH3:18])[CH:12]=[C:13]([O:15][CH3:16])[N:14]=2)=[O:7])(=[O:4])=[O:3])[CH2:24][CH2:25]1

Komponenten

7

Edukt 4

HCID 8471TriethylamineHCID 70918Chlorosulfonyl isocyanateHCID 1189462-Amino-4,6-dimethoxypyrimidineHCID 15278634o-Amino-alpha-cyclopropylbenzyl alcohol

Produkt 1

HCID 152786351-[(alpha-Cyclopropyl-alpha-hydroxy-o-tolyl)sulfamoyl]-3-(4,6-dimethoxy-2-pyrimidinyl)ureaAusbeute 21,3 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6344DichloromethaneLösungsmittel2×HCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

Chlorosulfonyl isocyanate (0.53 mL, 0.86 g, 6.1 mmol) is added to a solution of 2-amino-4,6-dimethoxypyrimidine (0.95 g, 6.1 mmol) in methylene chloride at 0° C. The resulting mixture is stirred for 30 minutes and a solution of o-amino-α-cyclopropylbenzyl alcohol (1.00 g, 6.1 mmol) and triethylamine (1.45 mL, 1.05 g, 10.4 mmol) in methylene chloride is slowly added to the mixture. The resulting solution is stirred at room temperature for hours, concentrated in vacuo and dissolved in methanol. The methanol solution is adjusted to about pH 1 with 10% hydrochloric acid and extracted with methylene chloride. The combined organic extracts are dried over anhydrous sodium sulfate and concentrated in vacuo to obtain a residue. Flash column chromatography of the residue using silica gel and 30% to 50% ethyl acetate in hexanes solutions gives the title product as a white solid (0.55 g, 21%, mp 66°-69° C.) which is identified by 1HNMR and MS spectral analyses.

Aufarbeitung

  1. stirringThe resulting solution is stirred at room temperature for hours
  2. concentrationconcentrated in vacuo
  3. dissolutiondissolved in methanol
  4. extractionextracted with methylene chloride
  5. dry with materialThe combined organic extracts are dried over anhydrous sodium sulfate
  6. concentrationconcentrated in vacuo
  7. customto obtain a residue

Quellen und Nachweise

ORD-Eintrag
ord-98214d620afa410490efb52acf386944
Quelldatensatz
uspto-grants-1995_11
Patentnummer
US05464808

Verknüpfte Notizen

Wird geladen…