Aniline → HCID 54204622, compound

HRID 1858296Notes

Reaction equation

[Si:1]([O:18][CH2:19][CH2:20][C:21]1[CH:22]=[C:23]([N:27]2[C:32]3=[N:33][C:34](S(C)(=O)=O)=[N:35][CH:36]=[C:31]3[CH2:30][N:29]([C:41]3[C:46]([Cl:47])=[CH:45][CH:44]=[CH:43][C:42]=3[Cl:48])[C:28]2=[O:49])[CH:24]=[CH:25][CH:26]=1)([C:14]([CH3:17])([CH3:16])[CH3:15])([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[NH2:50][C:51]1[CH:56]=[CH:55][CH:54]=[CH:53][CH:52]=1>Cl>[NH:50]([C:34]1[N:33]=[C:32]2[N:27]([C:23]3[CH:24]=[CH:25][CH:26]=[C:21]([CH2:20][CH2:19][O:18][Si:1]([C:14]([CH3:17])([CH3:16])[CH3:15])([C:8]4[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=4)[C:2]4[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=4)[CH:22]=3)[C:28](=[O:49])[N:29]([C:41]3[C:46]([Cl:47])=[CH:45][CH:44]=[CH:43][C:42]=3[Cl:48])[CH2:30][C:31]2=[CH:36][N:35]=1)[C:51]1[CH:56]=[CH:55][CH:54]=[CH:53][CH:52]=1

Participants

Conditions

Temperature: 100 °C

Procedure

A mixture of 980 mg (1.22 mmol) of 1-[3-(2-t-butyldiphenylsilyloxyethyl)phenyl]-3-(2,6-dichlorophenyl)-7-methanesulfonyl-3,4-dihydropyrimido[4,5-d]pyrimidin-2(1H)-one and 5 ml of aniline was heated at 100° C. for 30 minutes. The reaction was allowed to cool then poured into 50 ml of 2M hydrochloric acid. The product was collected by filtration, washed with water (50 ml), then hexane (50 ml) and dried to give 960 mg (96%) of 7-anilino-1-[3-(2-tert-butyldiphenylsilyloxyethyl)phenyl]-3-(2,6-dichlorophenyl)-3,4-dihydro-pyrimido[4,5-d]pyrimidin-2(1H)-one as a fawn solid. [Mass spectrum (ESI) MH+ =744].

Workup

temperatureto cool
filtrationThe product was collected by filtration
washwashed with water (50 ml)
dry with materialhexane (50 ml) and dried

Sources & evidence

ORD record: ord-51c2792cf8be40d090b8ee93b3824964
Source dataset: uspto-grants-2000_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06150373

Reaction notes

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