2-(Methylsulfanyl)-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine → (S)-1-cyclopropyl-3-(4-(2-(3-methylmorpholino)-6-(2-(methylthio)pyridin-3-yl)pyrimidin-4-yl)phenyl)urea

HRID 1771535Notes

Reaction equation

HRID 1771535 reaction equation
FC1C=C(C2N=C(SC)N=C(N3CCOC[C@@H]3C)C=2)C=NC=1.Cl[C:24]1[N:29]=[C:28]([N:30]2[CH2:35][CH2:34][O:33][CH2:32][C@@H:31]2[CH3:36])[N:27]=[C:26]([C:37]2[CH:42]=[CH:41][C:40]([NH:43][C:44]([NH:46][CH:47]3[CH2:49][CH2:48]3)=[O:45])=[CH:39][CH:38]=2)[CH:25]=1.[CH3:50][S:51][C:52]1[C:57](B2OC(C)(C)C(C)(C)O2)=[CH:56][CH:55]=[CH:54][N:53]=1>>[CH:47]1([NH:46][C:44]([NH:43][C:40]2[CH:41]=[CH:42][C:37]([C:26]3[CH:25]=[C:24]([C:57]4[C:52]([S:51][CH3:50])=[N:53][CH:54]=[CH:55][CH:56]=4)[N:29]=[C:28]([N:30]4[CH2:35][CH2:34][O:33][CH2:32][C@@H:31]4[CH3:36])[N:27]=3)=[CH:38][CH:39]=2)=[O:45])[CH2:49][CH2:48]1

Participants

4

Reactant 3

HCID 447551872-(Methylsulfanyl)-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridineHCID 67382782(S)-4-(6-(5-fluoropyridin-3-yl)-2-(methylthio)pyrimidin-4-yl)-3-methylmorpholineHCID 86691158HCID 86691158, compound2×

Product 1

HCID 67382676(S)-1-cyclopropyl-3-(4-(2-(3-methylmorpholino)-6-(2-(methylthio)pyridin-3-yl)pyrimidin-4-yl)phenyl)ureaYield 65%

Procedure

Method as described for intermediate 5 using (S)-1-(4-(6-chloro-2-(3-methylmorpholino)pyrimidin-4-yl)phenyl)-3-cyclopropylurea (intermediate 22) and 2-(methylsulfanyl)pyridine-3-boronic acid pinacol ester to afford a yellow solid (160 mg, 65%).

Sources & evidence

ORD record
ord-04d2431b464b418b8248540c919a3e5b
Source dataset
uspto-grants-2016_02
Patent number
US09249129B2

Reaction notes

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