Aniline → HCID 22125042, compound

HRID 1858333Notes

Reaction equation

[Cl:1][C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[CH:4][C:3]=1[N:9]1[CH2:18][C:17]2[C:12](=[N:13][C:14](S(C)(=O)=O)=[N:15][CH:16]=2)[N:11]([C:23]2[CH:24]=[C:25]([CH2:29][CH2:30][CH2:31][N:32]3[C:40](=[O:41])[C:39]4[C:34](=[CH:35][CH:36]=[CH:37][CH:38]=4)[C:33]3=[O:42])[CH:26]=[CH:27][CH:28]=2)[C:10]1=[O:43].[NH2:44][C:45]1[CH:50]=[CH:49][CH:48]=[CH:47][CH:46]=1>Cl>[Cl:1][C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[CH:4][C:3]=1[N:9]1[CH2:18][C:17]2[C:12](=[N:13][C:14]([NH:44][C:45]3[CH:50]=[CH:49][CH:48]=[CH:47][CH:46]=3)=[N:15][CH:16]=2)[N:11]([C:23]2[CH:24]=[C:25]([CH2:29][CH2:30][CH2:31][N:32]3[C:40](=[O:41])[C:39]4[C:34](=[CH:35][CH:36]=[CH:37][CH:38]=4)[C:33]3=[O:42])[CH:26]=[CH:27][CH:28]=2)[C:10]1=[O:43]

Participants

Conditions

Temperature: 140 °C

Procedure

A mixture of 190 mg (0.3 mmol) of 2-[3-[3-[3-(2,4-dichlorophenyl)-7-methanesulfonyl-2-oxo-3,4-dihydro-2H-pyrimido[4,5-d]pyrimidin-1-yl]-phenyl]-propyl]-isoindole-1,3-dione and 1 ml of aniline was heated at 140° C. for 35 minutes and then cooled. The mixture was added to 40 ml of 2M aqueous hydrochloric acid and the precipitated product was filtered off, washed with 2M aqueous hydrochloric acid, then with water and finally dried to give 200 mg (100%) of 2-[3-[3-[3-(2,4-dichlorophenyl)-2-oxo-7-phenylamino-3,4-dihydro-2H-pyrimido[4,5-d]pyrimidin-1-yl]-phenyl]-propyl]-isoindole-1,3-dione as a pale brown solid. [Mass spectrum (ESI) MH+ =649].

Workup

temperaturecooled
filtrationthe precipitated product was filtered off
washwashed with 2M aqueous hydrochloric acid
dry with materialwith water and finally dried

Sources & evidence

ORD record: ord-e0458ee97d504aca89b3a808f5acc052
Source dataset: uspto-grants-2000_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06150373

Reaction notes

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