Aniline → 6-((4-Pyridin-2yl)-benzyl)-1-isobutyl-3-methyl-5-(phenylamino)-1H-pyrrolo[3,4-d]pyrimidine-2,4(3H,6H)-dione

HRID 1423004Notes

Reaction equation

HRID 1423004 reaction equation
Cl[C:2]1[N:3]([CH2:18][C:19]2[CH:24]=[CH:23][C:22]([C:25]3[CH:30]=[CH:29][CH:28]=[CH:27][N:26]=3)=[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].[NH2:31][C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1>>[N:26]1[CH:27]=[CH:28][CH:29]=[CH:30][C:25]=1[C:22]1[CH:21]=[CH:20][C:19]([CH2:18][N:3]2[C:2]([NH:31][C:32]3[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=3)=[C:10]3[C:5]([N:6]([CH2:14][CH:15]([CH3:17])[CH3:16])[C:7](=[O:13])[N:8]([CH3:12])[C:9]3=[O:11])=[CH:4]2)=[CH:24][CH:23]=1

Participants

3

Reactant 2

HCID 6115AnilineHCID 67416103HCID 67416103, compound

Product 1

HCID 462342776-((4-Pyridin-2yl)-benzyl)-1-isobutyl-3-methyl-5-(phenylamino)-1H-pyrrolo[3,4-d]pyrimidine-2,4(3H,6H)-dioneYield 46%

Conditions

Temperature
150 °C

Procedure

Crude 5-chloro-1-isobutyl-3-methyl-6-(4-(pyridin-2-yl)benzyl)-1H-pyrrolo[3,4-d]pyrimidine-2,4(3H,6H)-dione (0.032 mmol) is placed in a Biotage microwave tube, and then aniline (0.2 mL) is added. The mixture is heated at 150° C. for an hour, and then purified by a semi-preparative HPLC to give 7 mg of pure product (overall yield:46%). MS (ESI) m/z 480.2 [M+H]+.

Workup

  1. custompurified by a semi-preparative HPLC

Sources & evidence

ORD record
ord-c9a8ab2fb86a4e0a848a8a7c6d07133d
Source dataset
uspto-grants-2015_01
Patent number
US08927556B2

Reaction notes

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