Aniline → 1-isobutyl-6-(4-methoxybenzyl)-3,7-dimethyl-5-(phenylamino)-1H-pyrrolo[3,4-d]pyrimidine-2,4(3H,6H)-dione

HRID 1423008Notes

Reaction equation

HRID 1423008 reaction equation
Cl[C:2]1[N:3]([CH2:19][C:20]2[CH:25]=[CH:24][C:23]([O:26][CH3:27])=[CH:22][CH:21]=2)[C:4]([CH3:18])=[C:5]2[C:10]=1[C:9](=[O:11])[N:8]([CH3:12])[C:7](=[O:13])[N:6]2[CH2:14][CH:15]([CH3:17])[CH3:16].[NH2:28][C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1>>[CH2:14]([N:6]1[C:5]2=[C:4]([CH3:18])[N:3]([CH2:19][C:20]3[CH:25]=[CH:24][C:23]([O:26][CH3:27])=[CH:22][CH:21]=3)[C:2]([NH:28][C:29]3[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=3)=[C:10]2[C:9](=[O:11])[N:8]([CH3:12])[C:7]1=[O:13])[CH:15]([CH3:17])[CH3:16]

Participants

3

Reactant 2

HCID 6115AnilineHCID 686249505-chloro-1-isobutyl-6-(4-methoxybenzyl)-3,7-dimethyl-1H-pyrrolo[3,4-d]pyrimidine-2,4(3H,6H)-dione

Product 1

HCID 462344311-isobutyl-6-(4-methoxybenzyl)-3,7-dimethyl-5-(phenylamino)-1H-pyrrolo[3,4-d]pyrimidine-2,4(3H,6H)-dione

Conditions

Temperature
150 °C

Procedure

5-chloro-1-isobutyl-6-(4-methoxybenzyl)-3,7-dimethyl-1H-pyrrolo[3,4-d]pyrimidine-2,4(3H,6H)-dione (12 mg, 0.03 mmol) is placed in a Biotage microwave tube, and then aniline (0.22 mL) is added. The mixture was heated at 150° C. for 3 h., and then purified by a semi-preparative HPLC to give 4 mg of pure product. MS (ESI) m/z 447.3 [M+H]+.

Workup

  1. custompurified by a semi-preparative HPLC

Sources & evidence

ORD record
ord-56948c7180b94923b48975de6cb18475
Source dataset
uspto-grants-2015_01
Patent number
US08927556B2

Reaction notes

Loading…