Reaktion #215714

Reaktionsgleichung

Chlorosulfonyl isocyanate

2-amino-4,6-dimethoxypyrimidine

o-amino-α-cyclopropylbenzyl alcohol

triethylamine

→

title product

Ausbeute 21.3%

1-[(α-cyclopropyl-α-hydroxy-o-tolyl)sulfamoyl]-3-(4,6-dimethoxy-2-pyrimidinyl)urea

Ausbeute 21.3%

Lösungsmittel

methylene chloride

—

hexanes

ethyl acetate

methylene chloride

Reaktionsbedingungen

Aufarbeitung

1. 1
   workup.STIRRINGThe resulting solution is stirred at room temperature for hours
2. 2
   Einengenconcentrated in vacuo
3. 3
   workup.DISSOLUTIONdissolved in methanol
4. 4
   Extraktionextracted with methylene chloride
5. 5
   TrocknenThe combined organic extracts are dried over anhydrous sodium sulfate
6. 6
   Einengenconcentrated in vacuo
7. 7
   Sonstigeto obtain a residue

Vorschrift

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.

Quelle