4,6-Dichloro-2-(methylthio)pyrimidine → 4-Chloro-6-(5-fluoro-2-(methylthio)phenyl)-2-(methylthio)pyrimidine

HRID 1771567Notes

Reaction equation

HRID 1771567 reaction equation
FC1C=C(C2N=C(SC)N=C(N3CCOC[C@@H]3C)C=2)C=NC=1.[Cl:23][C:24]1[CH:29]=[C:28](Cl)[N:27]=[C:26]([S:31][CH3:32])[N:25]=1.[F:33][C:34]1[CH:35]=[CH:36][C:37]([S:43][CH3:44])=[C:38](B(O)O)[CH:39]=1>>[Cl:23][C:24]1[CH:29]=[C:28]([C:36]2[CH:35]=[C:34]([F:33])[CH:39]=[CH:38][C:37]=2[S:43][CH3:44])[N:27]=[C:26]([S:31][CH3:32])[N:25]=1

Participants

4

Reactant 3

HCID 805314,6-Dichloro-2-(methylthio)pyrimidineHCID 532163695-Fluoro-2-(methylthio)phenylboronic acidHCID 67382782(S)-4-(6-(5-fluoropyridin-3-yl)-2-(methylthio)pyrimidin-4-yl)-3-methylmorpholine

Product 1

HCID 866911544-Chloro-6-(5-fluoro-2-(methylthio)phenyl)-2-(methylthio)pyrimidine

Procedure

Method as described for intermediate 5 using 4,6-dichloro-2-(methylthio)pyrimidine and 5-fluoro-2-(methylthio)phenylboronic acid. The residue was purified further by flash chromatography (0-10% EtOAc in petroleum ether (40:60) to afford 4-chloro-6-(5-fluoro-2-(methylthio)phenyl)-2-(methylthio)pyrimidine as a white solid, (500 mg, 42%)

Workup

  1. customThe residue was purified further by flash chromatography (0-10% EtOAc in petroleum ether (40:60)

Sources & evidence

ORD record
ord-cbbe021f6c064c1b81a9cdd560c897b9
Source dataset
uspto-grants-2016_02
Patent number
US09249129B2

Reaction notes

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