Acryloyl chloride → HCID 72944768, compound

HRID 2404014Notes

Reaction equation

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

Participants

Conditions

Temperature: 0 °C

Procedure

2-(2-amino-6-methylphenylamino)-6-(2,6-dichloro-3,5-dimethoxyphenyl)-8-methylpyrido[2,3-d]pyrimidin-7(8H)-one (11) was taken up in DCM (2 ml) and cooled to 0° C., followed by addition of acryloyl chloride (0.010 mL, 0.13 mmol). The reaction was allowed to warm to room temperature and stirred overnight. The mixture was loaded directly onto silica gel and purified by flash chromatography using 0-100% EtOAc/Hexanes gradient to provide the product, N-(2-((6-(2,6-dichloro-3,5-dimethoxyphenyl)-8-methyl-7-oxo-7,8-dihydropyrido[2,3-d]pyrimidin-2-yl)amino)-3-methylphenyl)acrylamide (Compound E). The product was obtained as an off-white solid (10 mg; 19% yield). MS (ES+) C26H23Cl2N5O4, 540 [M+H]+.

Workup

temperatureto warm to room temperature
custompurified by flash chromatography

Sources & evidence

ORD record: ord-fac620d8cf334c11b836f69a44dc2293
Source dataset: uspto-grants-2014_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08802697B2

Reaction notes

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