Reaction #303326

Reaction equation

acetamide oxime

TBTU

3-{2-methoxy-6-[2-(4-methoxy-phenyl)-ethylamino]-pyrimidin-4-yl}-benzoic acid

diisopropylethylamine

→

N-(1-imino-ethyl)-3-{2-methoxy-6-[2-(4-methoxy-phenyl)-ethylamino]-pyrimidin-4-yl}-benzamide

Yield 69.0%

Solvents

water

dimethylformamide

Conditions

Workup

1. 1
   workup.STIRRINGAfter 4 hours of stirring at ambient temperature the mixture
2. 2
   Extractionextracted twice with EtOAc (20 mL)
3. 3
   WashThe combined organic extracts are washed three times with water (20 mL)
4. 4
   Dryingwith brine (20 mL), dried over magnesium sulfate
5. 5
   Filtrationfiltered
6. 6
   Concentrationconcentrated by rotary evaporator

Procedure

To a solution of 3-{2-methoxy-6-[2-(4-methoxy-phenyl)-ethylamino]-pyrimidin-4-yl}-benzoic acid (200 mg, 0.53 mmol, Example 35(a)] in dimethylformamide (1.75 mL) is added diisopropylethylamine (0.23 mL, 1.33 mmol) followed by TBTU (205 mg, 0.64 mmol). Stirred the solution for 15 minutes before adding acetamide oxime (59 mg, 0.8 mmol). After 4 hours of stirring at ambient temperature the mixture is diluted with water (20 mL) and extracted twice with EtOAc (20 mL). The combined organic extracts are washed three times with water (20 mL), with brine (20 mL), dried over magnesium sulfate, filtered and concentrated by rotary evaporator to provide N-(1-imino-ethyl)-3-{2-methoxy-6-[2-(4-methoxy-phenyl)-ethylamino]-pyrimidin-4-yl}-benzamide [60 mg, 69%, Intermediate (45)].

Source