Réaction #324416

Équation de réaction

3-benzyl-5-(4-methoxyphenyl)pyrazin-2-amine

4-methoxyphenyl isocyanate

→

Compound 11u

Rendement 59.2%

1-[3-Benzyl-5-(4-methoxyphenyl)pyrazin-2-yl]-3-(4-methoxyphenyl)urea

Rendement 59.2%

Solvants

1,2-dichloroethane

Conditions de réaction

Traitement

1. 1
   Températurethe mixture was heated
2. 2
   TempératureAfter cooling to room temperature
3. 3
   Autrethe solid precipitated
4. 4
   Filtrationwas collected by filtration
5. 5
   Autredried in vacuo
6. 6
   Autreto give the crude product (293 mg, <664 μmol, <63.2%) as a colorless solid
7. 7
   AutreAn aliquot (93.0 mg, <211 μmol) was recrystallized from methanol

Mode opératoire

Under an argon atmosphere, to a solution of 3-benzyl-5-(4-methoxyphenyl)pyrazin-2-amine (12) (synthesized by the process of M. Adamczyk, et al., Org. Prep. Proced. Int., 33, 477-485 (2001)) (306 mg, 1.05 mmol) in anhydrous 1,2-dichloroethane (10 mL) was added 4-methoxyphenyl isocyanate (13) (191 μL, 1.00 mmol) at room temperature, and the mixture was heated with stirring at 80° C. for 19 hours. After cooling to room temperature, the solid precipitated was collected by filtration and dried in vacuo to give the crude product (293 mg, <664 μmol, <63.2%) as a colorless solid. An aliquot (93.0 mg, <211 μmol) was recrystallized from methanol to give Compound 11u (54.9 mg, 125 μmol, 59.2%) as a colorless solid. Rf=0.50 (n-hexane/ethyl acetate=1/1); 1H NMR (400 MHz, DMSO-d6) δ 3.73 (s, 3H), 3.81 (s, 3H), 4.36 (s, 2H), 6.98-6.93 (AA′BB′, 2H), 7.02-7.08 (AA′BB′, 2H), 7.17-7.25 (m, 1H), 7.28-7.32 (m, 4H), 7.43-7.48 (AA′BB′, 2H), 7.95-8.01 (AA′BB′, 2H), 8.79 (s, 1H), 9.04 (s, 1H), 10.58 (s, 1H); 13C NMR (67.8 MHz, DMSO-d6) δ 38.5, 55.18, 55.24, 114.0 (2C), 114.4 (2C), 121.1 (2C), 126.3, 127.2 (2C), 128.2, 128.3 (2C), 129.0 (2C), 131.7, 134.5, 137.9, 144.4, 145.0, 145.4, 152.2, 155.1, 160.1; IR (KBr, cm−1) 704, 746, 824, 1038, 1173, 1242, 1329, 1369, 1416, 1481, 1510, 1570, 1607, 1668, 2833, 3030, 3261; Anal. Calcd. For C26H24N4O3: C, 70.89; H, 5.49; N, 12.72. Found: C, 70.66; H, 5.49; N, 12.61.

Source