Dichloromethane → (S)-4-(4-(5-fluoro-2-(methylsulfonyl)phenyl)-6-(3-methylmorpholino)pyrimidin-2-yl)aniline

HRID 1771541Notes

Reaction equation

Cl[C:2]1[N:7]=[C:6]([N:8]2[CH2:13][CH2:12][O:11][CH2:10][C@@H:9]2[CH3:14])[CH:5]=[C:4]([C:15]2[CH:20]=[C:19]([F:21])[CH:18]=[CH:17][C:16]=2[S:22]([CH3:25])(=[O:24])=[O:23])[N:3]=1.CC1(C)C(C)(C)OB([C:34]2[CH:40]=[CH:39][C:37]([NH2:38])=[CH:36][CH:35]=2)O1.C(Cl)Cl.C([O-])([O-])=O.[Na+].[Na+]>COCCOC.O.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>[F:21][C:19]1[CH:18]=[CH:17][C:16]([S:22]([CH3:25])(=[O:24])=[O:23])=[C:15]([C:4]2[CH:5]=[C:6]([N:8]3[CH2:13][CH2:12][O:11][CH2:10][C@@H:9]3[CH3:14])[N:7]=[C:2]([C:34]3[CH:40]=[CH:39][C:37]([NH2:38])=[CH:36][CH:35]=3)[N:3]=2)[CH:20]=1

Participants

Conditions

Temperature: 120 °C

Procedure

(S)-4-(2-chloro-6-(5-fluoro-2-(methylsulfonyl)phenyl)pyrimidin-4-yl)-3-methylmorpholine (intermediate 10) (350 mg, 0.91 mmol), 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)aniline (239 mg, 1.09 mmol), Pd(PPh3)2Cl2.DCM (37 mg, 0.05 mmol) and Na2CO3 (145 mg, 1.36 mmol) were dissolved in a mixture of DME:H2O (4:1) and stirred at 120° C. under microwave for 30 mins. The reaction mixture was partitioned between H2O and DCM. The organic layer was recovered, dried over MgSO4, filtered and the solvent removed in vacuo to yield the title compound as a brown solid (128 mg, 0.29 mmol, 32% yield).

Workup

customThe reaction mixture was partitioned between H2O and DCM
customThe organic layer was recovered
dry with materialdried over MgSO4
filtrationfiltered
customthe solvent removed in vacuo

Sources & evidence

ORD record: ord-917551fa02e4402ca313c3ad97f7ab79
Source dataset: uspto-grants-2016_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09249129B2

Reaction notes

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