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

HRID 707451Notes

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][NH:17][C:18]([NH:20][C:21]1[CH:26]=[CH:25][C:24](B2OC(C)(C)C(C)(C)O2)=[CH:23][CH:22]=1)=[O:19].C([O-])([O-])=O.[Na+].[Na+]>COCCOC.C(Cl)Cl>[Cl:8][C:6]1[N:5]=[C:4]([N:9]2[CH2:14][CH2:13][O:12][CH2:11][C@@H:10]2[CH3:15])[N:3]=[C:2]([C:24]2[CH:23]=[CH:22][C:21]([NH:20][C:18]([NH:17][CH3:16])=[O:19])=[CH:26][CH:25]=2)[N:7]=1

Participants

Conditions

Temperature: 90 °C

Procedure

A mixture of (S)-4-(4,6-dichloro-1,3,5-triazin-2-yl)-3-methylmorpholine (step (i) example 1) (4 g, 16.1 mmol), 1-methyl-3-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)urea (4.67 g, 16.1 mmol), bis(triphenylphosphene)palladium(II) dichloride (0.66 g, 0.8 mmol) and 2M Na2CO3 (8 ml, 19.6 mmol) in DME (32 ml) was heated in the microwave at 90° C. for 90 minutes. The mixture was 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 black oil. The oil was purified by flash chromatography using Pet ether, EtOAc 0-100% gradient to yield an off-white solid of (S)-1-(4-(4-chloro-6-(3-methylmorpholino)-1,3,5-triazin-2-yl)phenyl)-3-methylurea. (932 mg, 15%)

Workup

washwashed with water (200 mL)
customthe solvent removed in vacuo
customto yield a black oil
customThe oil was purified by flash chromatography

Sources & evidence

ORD record: ord-09131d15952146e6b0b609a250000007
Source dataset: uspto-grants-2015_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09175011B2

Reaction notes

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