2-(Methylsulfonyl)phenylboronic Acid → 1-Ethyl-3-(4-(6-(2-(methylsulfonyl)phenyl)-2-morpholinopyrimidin-4-yl)phenyl)urea

HRID 1771547Notes

Reaction equation

HRID 1771547 reaction equation
Cl[C:2]1[N:7]=[C:6]([N:8]2[CH2:13][CH2:12][O:11][CH2:10][CH2:9]2)[N:5]=[C:4]([C:14]2[CH:19]=[CH:18][C:17]([NH:20][C:21]([NH:23][CH2:24][CH3:25])=[O:22])=[CH:16][CH:15]=2)[CH:3]=1.[CH3:26][S:27]([C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][C:31]=1B(O)O)(=[O:29])=[O:28]>>[CH2:24]([NH:23][C:21]([NH:20][C:17]1[CH:18]=[CH:19][C:14]([C:4]2[CH:3]=[C:2]([C:31]3[CH:32]=[CH:33][CH:34]=[CH:35][C:30]=3[S:27]([CH3:26])(=[O:29])=[O:28])[N:7]=[C:6]([N:8]3[CH2:13][CH2:12][O:11][CH2:10][CH2:9]3)[N:5]=2)=[CH:15][CH:16]=1)=[O:22])[CH3:25]

Participants

3

Reactant 2

HCID 27735392-(Methylsulfonyl)phenylboronic AcidHCID 866911511-(4-(6-Chloro-2-morpholinopyrimidin-4-yl)phenyl)-3-ethylurea

Product 1

HCID 533806371-Ethyl-3-(4-(6-(2-(methylsulfonyl)phenyl)-2-morpholinopyrimidin-4-yl)phenyl)ureaYield 10%

Procedure

Method as described for Example 8 using 1-(4-(6-chloro-2-morpholinopyrimidin-4-yl)phenyl)-3-ethylurea and (2-methylsulfonylphenyl)boronic acid. The reaction mixture was concentrated in vacuo, and the residue dissolved in DMSO, filtered and purified by prep HPLC (low pH) to afford a white solid (13.2 mg, 10%).

Workup

  1. concentrationThe reaction mixture was concentrated in vacuo
  2. dissolutionthe residue dissolved in DMSO
  3. filtrationfiltered
  4. custompurified by prep HPLC (low pH)

Sources & evidence

ORD record
ord-c6fb2cf59ca84cb5b744afecb272d1e6
Source dataset
uspto-grants-2016_02
Patent number
US09249129B2

Reaction notes

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