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)pyrimidin-2-yl)phenyl)urea

HRID 1771561Notes

Reaction equation

HRID 1771561 reaction equation
Cl[C:2]1[N:7]=[C:6]([N:8]2[CH2:13][CH2:12][O:11][CH2:10][C@@H:9]2[CH3:14])[CH:5]=[CH:4][N:3]=1.[OH:15][CH2:16][CH2:17][NH:18][C:19]([NH:21][C:22]1[CH:27]=[CH:26][C:25](B2OC(C)(C)C(C)(C)O2)=[CH:24][CH:23]=1)=[O:20]>>[OH:15][CH2:16][CH2:17][NH:18][C:19]([NH:21][C:22]1[CH:27]=[CH:26][C:25]([C:2]2[N:7]=[C:6]([N:8]3[CH2:13][CH2:12][O:11][CH2:10][C@@H:9]3[CH3:14])[CH:5]=[CH:4][N:3]=2)=[CH:24][CH:23]=1)=[O:20]

Participants

3

Reactant 2

HCID 446073541-(2-Hydroxyethyl)-3-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)urea2×HCID 72942067(S)-4-(2-Chloropyrimidin-4-yl)-3-methylmorpholine2×

Product 1

HCID 53379561(S)-1-(2-hydroxyethyl)-3-(4-(4-(3-methylmorpholino)pyrimidin-2-yl)phenyl)urea

Procedure

Method as described for example 49 using (S)-4-(2-chloropyrimidin-4-yl)-3-methylmorpholine (intermediate 3) and 1-(2-hydroxyethyl)-3-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)urea (intermediate 18). The mixture was purified by prep HPLC at high pH to afford the title compound. (24 mg, 15%).

Workup

  1. customThe mixture was purified by prep HPLC at high pH

Sources & evidence

ORD record
ord-96584ba16b59426eb178709892b4fe50
Source dataset
uspto-grants-2016_02
Patent number
US09249129B2

Reaction notes

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