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

HRID 1771553Notes

Reaction equation

HRID 1771553 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.[CH:37]1([NH:40][C:41](=[O:58])[NH:42][C:43]2[CH:48]=[CH:47][C:46](B3OC(C)(C)C(C)(C)O3)=[CH:45][CH:44]=2)[CH2:39][CH2:38]1>>[CH:37]1([NH:40][C:41]([NH:42][C:43]2[CH:48]=[CH:47][C:46]([C:24]3[CH:29]=[CH:28][N:27]=[C:26]([N:30]4[CH2:35][CH2:34][O:33][CH2:32][C@@H:31]4[CH3:36])[N:25]=3)=[CH:45][CH:44]=2)=[O:58])[CH2:39][CH2:38]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 87379247(S)-4-(4-chloropyrimidin-2-yl)-3-methylmorpholine2×

Product 1

HCID 53380860(S)-1-cyclopropyl-3-(4-(2-(3-methylmorpholino)pyrimidin-4-yl)phenyl)ureaYield 66%

Procedure

Method as described for intermediate 5 using (S)-4-(4-chloropyrimidin-2-yl)-3-methylmorpholine (intermediate 15) and 4-(3-cyclopropylureido)phenyl boronic acid pinacol ester. Material was purified using flash chromatography (20-90% EtOAc in petroleum ether 40-60) to afford a light pink solid (130 mg, 66%).

Workup

  1. customMaterial was purified

Sources & evidence

ORD record
ord-892f495c659f410e96e7f207009928b4
Source dataset
uspto-grants-2016_02
Patent number
US09249129B2

Reaction notes

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