N-Ethyl-N'-[4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]urea → (S)-1-ethyl-3-(4-(2-(3-methylmorpholino)pyrimidin-4-yl)phenyl)urea

HRID 1771552Notes

Reaction equation

HRID 1771552 reaction equation
FC1C=C(C2N=C(SC)N=C(N3CCOC[C@@H]3C)C=2)C=NC=1.Cl[C:24]1[CH:29]=[CH:28][N:27]=[C:26]([N:30]2[CH2:35][CH2:34][O:33][CH2:32][C@@H:31]2[CH3:36])[N:25]=1.[CH2:37]([NH:39][C:40](=[O:57])[NH:41][C:42]1[CH:47]=[CH:46][C:45](B2OC(C)(C)C(C)(C)O2)=[CH:44][CH:43]=1)[CH3:38]>>[CH2:37]([NH:39][C:40]([NH:41][C:42]1[CH:47]=[CH:46][C:45]([C:24]2[CH:29]=[CH:28][N:27]=[C:26]([N:30]3[CH2:35][CH2:34][O:33][CH2:32][C@@H:31]3[CH3:36])[N:25]=2)=[CH:44][CH:43]=1)=[O:57])[CH3:38]

Participants

4

Reactant 3

HCID 44119377N-Ethyl-N'-[4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]ureaHCID 67382782(S)-4-(6-(5-fluoropyridin-3-yl)-2-(methylthio)pyrimidin-4-yl)-3-methylmorpholineHCID 87379247(S)-4-(4-chloropyrimidin-2-yl)-3-methylmorpholine2×

Product 1

HCID 53380859(S)-1-ethyl-3-(4-(2-(3-methylmorpholino)pyrimidin-4-yl)phenyl)urea

Procedure

Method as described for intermediate 5 using (S)-4-(4-chloropyrimidin-2-yl)-3-methylmorpholine (intermediate 15) and 4-(3-ethylureido)phenyl boronic acid pinacol ester. Material was purified by prep HPLC (low pH) to afford a brown solid, (77 mg, 40%).

Workup

  1. customMaterial was purified by prep HPLC (low pH)
  2. customto afford a brown solid, (77 mg, 40%)

Sources & evidence

ORD record
ord-521b90b51ac44693a03b392f5634143d
Source dataset
uspto-grants-2016_02
Patent number
US09249129B2

Reaction notes

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