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

HRID 1423001Notes

Reaction equation

HRID 1423001 reaction equation
Cl[C:2]1[N:3]([CH2:18][C:19]2[CH:24]=[CH:23][C:22]([O:25][CH3:26])=[CH:21][CH:20]=2)[CH:4]=[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].[NH2:27][C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1>>[CH2:14]([N:6]1[C:5]2=[CH:4][N:3]([CH2:18][C:19]3[CH:24]=[CH:23][C:22]([O:25][CH3:26])=[CH:21][CH:20]=3)[C:2]([NH:27][C:28]3[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=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 674146965-chloro-1-isobutyl-6-(4-methoxybenzyl)-3-methyl-1H-pyrrolo[3,4-d]pyrimidine-2,4(3H,6H)-dione

Product 1

HCID 462342761-Isobutyl-6-(4-methoxybenzyl)-3-methyl-5-(phenylamino)-1H-pyrrolo[3,4-d]pyrimidine-2,4(3H,6H)-dioneYield 120.2%

Conditions

Temperature
180 °C

Procedure

5-chloro-1-isobutyl-6-(4-methoxybenzyl)-3-methyl-1H-pyrrolo[3,4-d]pyrimidine-2,4(3H,6H)-dione (14 mg, 0.025 mmol) is placed in a Biotage microwave tube, and then aniline (0.5 mL, 5.4 mmol) is added. The mixture was heated at 180° C. for 4 h. The mixture is purified by a semi-preparative HPLC to give 13 mg of pure product (yield: 81%). MS (ESI) m/z 433.2 [M+H]+.

Workup

  1. customThe mixture is purified by a semi-preparative HPLC

Sources & evidence

ORD record
ord-475127fd32564974a3fc62a2bf798634
Source dataset
uspto-grants-2015_01
Patent number
US08927556B2

Reaction notes

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