4-(Tetramethyl-1,3,2-dioxaborolan-2-yl)aniline → (S)-4-(6-(5-fluoro-2-(methylsulfonyl)phenyl)-2-(3-methylmorpholino)pyrimidin-4-yl)aniline

HRID 1771540Notes

Reaction equation

HRID 1771540 reaction equation
F[C:2]1[CH:3]=[C:4]([C:8]2[N:13]=C(SC)N=[C:10](N3CCOC[C@@H]3C)[CH:9]=2)C=NC=1.Cl[C:24]1[CH:29]=[C:28]([C:30]2[CH:35]=[C:34]([F:36])[CH:33]=[CH:32][C:31]=2[S:37]([CH3:40])(=[O:39])=[O:38])[N:27]=[C:26]([N:41]2[CH2:46][CH2:45][O:44][CH2:43][C@@H:42]2[CH3:47])[N:25]=1.CC1(C)C(C)(C)OB(C2C=CC(N)=CC=2)O1>>[F:36][C:34]1[CH:33]=[CH:32][C:31]([S:37]([CH3:40])(=[O:39])=[O:38])=[C:30]([C:28]2[N:27]=[C:26]([N:41]3[CH2:46][CH2:45][O:44][CH2:43][C@@H:42]3[CH3:47])[N:25]=[C:24]([C:2]3[CH:3]=[CH:4][C:8]([NH2:13])=[CH:9][CH:10]=3)[CH:29]=2)[CH:35]=1

Participants

4

Reactant 3

HCID 27346204-(Tetramethyl-1,3,2-dioxaborolan-2-yl)anilineHCID 67382782(S)-4-(6-(5-fluoropyridin-3-yl)-2-(methylthio)pyrimidin-4-yl)-3-methylmorpholineHCID 86691148(S)-4-(4-chloro-6-(5-fluoro-2-(methylsulfonyl)phenyl)pyrimidin-2-yl)-3-methylmorpholine2×

Product 1

HCID 67382314(S)-4-(6-(5-fluoro-2-(methylsulfonyl)phenyl)-2-(3-methylmorpholino)pyrimidin-4-yl)anilineYield 58%

Procedure

Method as described for intermediate 5 using (S)-4-(4-chloro-6-(5-fluoro-2-(methylsulfonyl)phenyl)pyrimidin-2-yl)-3-methylmorpholine (intermediate 16) (451 mg, 1.17 mmol) and 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)aniline (256 mg, 1.17 mmol). The mixture was purified using flash chromatography (30-100% EtOAc in petroleum ether 40-60) to afford the title compound (298 mg, 58%)

Workup

  1. customThe mixture was purified

Sources & evidence

ORD record
ord-2bf03ae669c545088fc452884e520f1f
Source dataset
uspto-grants-2016_02
Patent number
US09249129B2

Reaction notes

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