Ethyl Acetate → HCID 72721606, compound

HRID 2280426Notes

Reaction equation

[Cl:1][C:2]1[N:7]=[C:6](Cl)[CH:5]=[CH:4][N:3]=1.Cl.[NH2:10][C:11]1[C:16]([CH3:17])=[CH:15][C:14](/[CH:18]=[CH:19]/[C:20]#[N:21])=[CH:13][C:12]=1[CH3:22].C(N(CC)C(C)C)(C)C.C(OCC)(=O)C>O>[Cl:1][C:2]1[N:7]=[C:6]([NH:10][C:11]2[C:16]([CH3:17])=[CH:15][C:14](/[CH:18]=[CH:19]/[C:20]#[N:21])=[CH:13][C:12]=2[CH3:22])[CH:5]=[CH:4][N:3]=1

Participants

Conditions

Temperature: 145 °C

Procedure

To a mixture of 2,4-dichloropyrimidine (25 gm) and (E)-3-(4-amino-3,5-dimethylphenyl)acrylonitrile hydrochloride (28 gm) was added N,N-diisopropylethylamine (250 ml) under stirring. The mixture was then heated to 140 to 150° C. and stirred for 55 to 60 hours. The solution was then cooled to room temperature and the solvent was distilled off under reduced pressure to provide a residual solid. To the residual solid was added ethyl acetate (1500 ml) and water (1000 ml). The reaction mass was stirred for 30 minutes at room temperature and then the layers were separated. The organic layer was dried with sodium sulfate and then concentrates to provide 30 gm of (E)-3-(4-(2-chloropyrimidin-4-ylamino)-3,5-dimethylphenyl)acrylonitrile.

Workup

stirringstirred for 55 to 60 hours
temperatureThe solution was then cooled to room temperature
distillationthe solvent was distilled off under reduced pressure
customto provide a residual solid
stirringThe reaction mass was stirred for 30 minutes at room temperature
customthe layers were separated
dry with materialThe organic layer was dried with sodium sulfate

Sources & evidence

ORD record: ord-27f820c4879c4be693fb42f8fd93ab1e
Source dataset: uspto-grants-2015_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09139535B2

Reaction notes

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