1-(2-Hydroxyethyl)-3-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)urea → (S)-1-(2-hydroxyethyl)-3-(4-(4-(3-methylmorpholino)-6-(pyridin-2-yl)pyrimidin-2-yl)phenyl)urea

HRID 1771557Notes

Reaction equation

HRID 1771557 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.[OH:43][CH2:44][CH2:45][NH:46][C:47]([NH:49][C:50]1[CH:55]=[CH:54][C:53](B2OC(C)(C)C(C)(C)O2)=[CH:52][CH:51]=1)=[O:48]>>[OH:43][CH2:44][CH2:45][NH:46][C:47]([NH:49][C:50]1[CH:55]=[CH:54][C:53]([C:24]2[N:29]=[C:28]([N:30]3[CH2:35][CH2:34][O:33][CH2:32][C@@H:31]3[CH3:36])[CH:27]=[C:26]([C:37]3[CH:42]=[CH:41][CH:40]=[CH:39][N:38]=3)[N:25]=2)=[CH:52][CH:51]=1)=[O:48]

Participants

4

Reactant 3

HCID 446073541-(2-Hydroxyethyl)-3-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)urea2×HCID 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 53379443(S)-1-(2-hydroxyethyl)-3-(4-(4-(3-methylmorpholino)-6-(pyridin-2-yl)pyrimidin-2-yl)phenyl)ureaYield 64%

Procedure

Method as described for intermediate 5 using (S)-4-(2-chloro-6-(pyridin-2-yl)pyrimidin-4-yl)-3-methylmorpholine (intermediate 21) and 1-(2-hydroxyethyl)-3-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)urea (intermediate 18). Material was purified by prep HPLC (low pH) to afford a grey solid. Further purification was achieved using an SCX-2 cartridge to afford a grey solid (122 mg, 64%).

Workup

  1. customMaterial was purified by prep HPLC (low pH)
  2. customto afford a grey solid
  3. customFurther purification

Sources & evidence

ORD record
ord-60436e5cbd0e48e295395e7bbfd0ec9b
Source dataset
uspto-grants-2016_02
Patent number
US09249129B2

Reaction notes

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