Reacción #330456

Ecuación de reacción

1-(3-phenylbenzo[b]thiophen-2-yl)ethylamine

1-(3-phenylbenzo[b]thiophen-2-yl)ethanamine

6-chloro-9H-purine

DIPEA

→

N-(1-(3-phenylbenzo[b]thiophen-2-yl)ethyl)-9H-purin-6-amine

Disolventes

n-butanol

Condiciones de reacción

Tratamiento posterior

1. 1
   TemperaturaAfter cooling to RT
2. 2
   Otrothe crude reaction mixture
3. 3
   Lavadowas washed with MeOH
4. 4
   Lavadothe product eluted with 2M NH3/MeOH
5. 5
   workup.ADDITIONThe product containing fractions
6. 6
   Concentraciónconcentrated in vacuo
7. 7
   Otrothe resulting residue was purified by column chromatography (Si—PCC, gradient 0-6% MeOH in DCM)
8. 8
   Otrotriturated with EtOAc affording 101 (105 mg, 45%)

Procedimiento

A mixture of 1-(3-phenylbenzo[b]thiophen-2-yl)ethylamine from Example 23 (160 mg, 0.63 mmol), 6-chloro-9H-purine (98 mg, 0.63 mmol) and DIPEA (0.16 mL, 0.95 mmol) in n-butanol (1.3 mL) was stirred in a sealed vial for 3 days at 120° C. After cooling to RT, the crude reaction mixture was loaded into an Isolute® SCX-2 which was washed with MeOH and the product eluted with 2M NH3/MeOH. The product containing fractions were combined and concentrated in vacuo and the resulting residue was purified by column chromatography (Si—PCC, gradient 0-6% MeOH in DCM) and then triturated with EtOAc affording 101 (105 mg, 45%). LCMS: RT 4.33 min [M+H]+ 372.1. 1H NMR (DMSO, 400 MHz): δ 8.21 (1H, s), 8.16-8.10 (2H, m), 7.92-7.86 (1H, m), 7.66-7.54 (4H, m), 7.50-7.44 (1H, m), 7.37-7.26 (3H, m), 5.76 (1H, s), 1.50 (3H, d, J=6.94 Hz)

Fuente