Sodium Carbonate → (S)-4-(4-chloro-6-(2-(methylsulfonyl)phenyl)-1,3,5-triazin-2-yl)-3-methylmorpholine

HRID 707450Notes

Reaction equation

Cl[C:2]1[N:7]=[C:6]([Cl:8])[N:5]=[C:4]([N:9]2[CH2:14][CH2:13][O:12][CH2:11][C@@H:10]2[CH3:15])[N:3]=1.[CH3:16][S:17]([C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][C:21]=1B(O)O)(=[O:19])=[O:18].C(=O)([O-])[O-].[Na+].[Na+]>COCCOC.O.C(Cl)Cl>[Cl:8][C:6]1[N:7]=[C:2]([C:21]2[CH:22]=[CH:23][CH:24]=[CH:25][C:20]=2[S:17]([CH3:16])(=[O:19])=[O:18])[N:3]=[C:4]([N:9]2[CH2:14][CH2:13][O:12][CH2:11][C@@H:10]2[CH3:15])[N:5]=1

Participants

Conditions

Temperature: 60 °C

Procedure

A mixture of (S)-4-(4,6-dichloro-1,3,5-triazin-2-yl)-3-methylmorpholine (1.25 g, 5.0 mmol), 2-methylsulfonylphenyl boronic acid (1.1 g, 5.5 mmol), sodium carbonate (1.6 g, 15.0 mmol) and bis(triphenylphosphene)palladium(II) dichloride (205 mg, 0.25 mmol) in DME/H2O/ (4:1, 10 mL) was heated in the microwave at 60° C. for 25 minutes. The mixture was then diluted with DCM (200 mL), washed with water (200 mL), the organic layer passed through a PTFE hydrophobic frit and the solvent removed in vacuo to yield a dark orange/brown oil (S)-4-(4-chloro-6-(2-(methylsulfonyl)phenyl)-1,3,5-triazin-2-yl)-3-methylmorpholine, 2.59 g, >100%, crude.

Workup

washwashed with water (200 mL)
customthe solvent removed in vacuo

Sources & evidence

ORD record: ord-7498068acaba4a06b7eb34d293919e28
Source dataset: uspto-grants-2015_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09175011B2

Reaction notes

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