Aniline → 1-(4-bromo-phenyl)-3-cyclopropyl-6,8-dimethyl-5-phenylamino-1H,8H-pyrido[2,3-d]pyrimidine-2,4,7-trione

HRID 75644Notes

Reaction equation

[Br:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[C:13]3[N:14]([CH3:31])[C:15](=[O:30])[C:16]([CH3:29])=[C:17](OS(C4C=CC(C)=CC=4)(=O)=O)[C:12]=3[C:11](=[O:32])[N:10]([CH:33]3[CH2:35][CH2:34]3)[C:9]2=[O:36])=[CH:4][CH:3]=1.[NH2:37][C:38]1[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=1>C(OCC)C.CCCCCC>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[C:13]3[N:14]([CH3:31])[C:15](=[O:30])[C:16]([CH3:29])=[C:17]([NH:37][C:38]4[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=4)[C:12]=3[C:11](=[O:32])[N:10]([CH:33]3[CH2:35][CH2:34]3)[C:9]2=[O:36])=[CH:4][CH:3]=1

Participants

Conditions

Temperature: 150 °C

Procedure

To toluene-4-sulfonic acid 1-(4-bromo-phenyl)-3-cyclopropyl-6,8-dimethyl-2,4,7-trioxo-1,2,3,4,7,8-hexahydro-pyrido[2,3-d]pyrimidin-5-yl ester 39 (100 mg) obtained in Step 6 was added aniline 40 (0.64 ml), and the mixture was stirred at 150° C. for 2.5 hrs. After allowing to cool to room temperature, diethyl ether-hexane [1:1 (volume ratio), 30 ml] was added to the reaction mixture, and the crystals were collected by filtration. The obtained crystals were purified by column chromatography (chloroform:acetone=15:1) to give 1-(4-bromo-phenyl)-3-cyclopropyl-6,8-dimethyl-5-phenylamino-1H,8H-pyrido[2,3-d]pyrimidine-2,4,7-trione 41 (81 mg, yield 93%) as pale-yellow crystals.

Workup

temperatureto cool to room temperature
filtrationthe crystals were collected by filtration
customThe obtained crystals were purified by column chromatography (chloroform:acetone=15:1)

Sources & evidence

ORD record: ord-b83be4e1390a4a33aec4d357aa866c2f
Source dataset: uspto-grants-2014_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08835443B2

Reaction notes

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