N-Cyclopropyl-N'-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)urea → (S)-1-cyclopropyl-3-(4-(4-(3-methylmorpholino)-6-(pyridin-2-yl)pyrimidin-2-yl)phenyl)urea

HRID 1771556Notes

Reaction equation

HRID 1771556 reaction equation
FC1C=C(C2N=C(SC)N=C(N3CCOC[C@@H]3C)C=2)C=NC=1.Cl[C:24]1[N:29]=[C:28]([N:30]2[CH2:35][CH2:34][O:33][CH2:32][C@@H:31]2[CH3:36])[CH:27]=[C:26]([C:37]2[CH:42]=[CH:41][CH:40]=[CH:39][N:38]=2)[N:25]=1.[CH:43]1([NH:46][C:47](=[O:64])[NH:48][C:49]2[CH:54]=[CH:53][C:52](B3OC(C)(C)C(C)(C)O3)=[CH:51][CH:50]=2)[CH2:45][CH2:44]1>>[CH:43]1([NH:46][C:47]([NH:48][C:49]2[CH:54]=[CH:53][C:52]([C:24]3[N:29]=[C:28]([N:30]4[CH2:35][CH2:34][O:33][CH2:32][C@@H:31]4[CH3:36])[CH:27]=[C:26]([C:37]4[CH:42]=[CH:41][CH:40]=[CH:39][N:38]=4)[N:25]=3)=[CH:51][CH:50]=2)=[O:64])[CH2:45][CH2:44]1

Participants

4

Reactant 3

HCID 44119149N-Cyclopropyl-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 86691152(S)-4-(2-chloro-6-(pyridin-2-yl)pyrimidin-4-yl)-3-methylmorpholine2×

Product 1

HCID 53379442(S)-1-cyclopropyl-3-(4-(4-(3-methylmorpholino)-6-(pyridin-2-yl)pyrimidin-2-yl)phenyl)urea

Procedure

Method as described for intermediate 5 using (S)-4-(2-chloro-6-(pyridin-2-yl)pyrimidin-4-yl)-3-methylmorpholine (intermediate 21) and 4-(3-cyclopropylureido)phenyl boronic acid pinacol ester. Material was purified by prep HPLC (low pH) to afford a light orange solid.

Workup

  1. customMaterial was purified by prep HPLC (low pH)
  2. customto afford a light orange solid

Sources & evidence

ORD record
ord-275ab3f445cf47eab959890850454bb7
Source dataset
uspto-grants-2016_02
Patent number
US09249129B2

Reaction notes

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