Diisopropylethylamine → HCID 118162173, compound

HRID 1749403Notes

Reaction equation

[C:1]1([CH3:16])[CH:6]=[CH:5][C:4]([O:7][C:8]2[C:13]([CH2:14][NH2:15])=[CH:12][N:11]=[CH:10][N:9]=2)=[CH:3][CH:2]=1.CCN(C(C)C)C(C)C.Cl[C:27]1[N:32]=[C:31]([Cl:33])[C:30]([C:34]([F:37])([F:36])[F:35])=[CH:29][N:28]=1>CN(C=O)C>[Cl:33][C:31]1[C:30]([C:34]([F:36])([F:35])[F:37])=[CH:29][N:28]=[C:27]([NH:15][CH2:14][C:13]2[C:8]([O:7][C:4]3[CH:3]=[CH:2][C:1]([CH3:16])=[CH:6][CH:5]=3)=[N:9][CH:10]=[N:11][CH:12]=2)[N:32]=1

Participants

Conditions

Temperature: -10 °C

Procedure

(4-(p-Tolyloxy)pyrimidin-5-yl)methanamine (1.0 equiv.) was placed in a round bottom flask with DIEA (1.0 equiv.), and DMF (0.4 M). The flask was placed in a cooling bath and cooled to −10° C. To the flask was added 2,4-dichloro-5-(trifluoromethyl)pyrimidine (1.0 equiv.) and stirring continued at −10° C. The reaction mixture was allowed to warm to room temperature over 3 h. The reaction mixture was loaded directly onto a silica gel column (100 g) and purified using 5-27% ethyl acetate in hexanes, followed by 27% ethyl acetate in hexanes. Fractions containing desired product (lower Rf spot by thin layer chromatography) were combined and the solvent was were removed under reduced pressure to give 4-chloro-N-((4-(p-tolyloxy)pyrimidin-5-yl)methyl)-5-(trifluoromethyl)pyrimidin-2-amine (27.0% yield) as a light yellow solid. MS (ESI) m/z 396.2 [M+1]+.

Workup

customThe flask was placed in a cooling bath
customcontinued at −10° C
temperatureto warm to room temperature over 3 h
custompurified
additionFractions containing desired product (lower Rf spot by thin layer chromatography)
customthe solvent was were removed under reduced pressure

Sources & evidence

ORD record: ord-59ec743fcf214197b02660b1f576eb70
Source dataset: uspto-grants-2015_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09156798B2

Reaction notes

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