Cesium carbonate → (S)-1-(4-(6-(2-cyanophenyl)-2-(3-methylmorpholino)pyrimidin-4-yl)phenyl)-3-ethylurea

HRID 1771545Notes

Reaction equation

HRID 1771545 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])[N:5]=[C:4]([C:15]2[CH:20]=[CH:19][C:18]([NH:21][C:22]([NH:24][CH2:25][CH3:26])=[O:23])=[CH:17][CH:16]=2)[CH:3]=1.[C:27]([C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][C:30]=1B(O)O)#[N:28].C(=O)([O-])[O-].[Cs+].[Cs+]>O1CCOCC1.O>[C:27]([C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][C:30]=1[C:2]1[N:7]=[C:6]([N:8]2[CH2:13][CH2:12][O:11][CH2:10][C@@H:9]2[CH3:14])[N:5]=[C:4]([C:15]2[CH:20]=[CH:19][C:18]([NH:21][C:22]([NH:24][CH2:25][CH3:26])=[O:23])=[CH:17][CH:16]=2)[CH:3]=1)#[N:28]

Participants

5

Reactant 3

HCID 10796Cesium carbonateHCID 27346102-Cyanophenylboronic acidHCID 86691150(S)-1-(4-(6-chloro-2-(3-methylmorpholino)pyrimidin-4-yl)phenyl)-3-ethylurea2×

Product 1

HCID 53380424(S)-1-(4-(6-(2-cyanophenyl)-2-(3-methylmorpholino)pyrimidin-4-yl)phenyl)-3-ethylureaYield 41.4%

Reagents, catalysts & solvents 1

HCID 218864351,4-Dioxane--water (1/1)Solvent

Procedure

(S)-1-(4-(6-chloro-2-(3-methylmorpholino)pyrimidin-4-yl)phenyl)-3-ethylurea (Intermediate 2) (90 mg, 0.24 mmol), 2-cyanobenzeneboronic acid (43 mg, 0.29 mmol), cesium carbonate (235 mg, 0.72 mmol) and bis(diphenylphosphino)-ferrocenedichloropalladium(II)-DCM-complex (10 mg, 0.01 mmol) in dioxane/water (1:3, 1 mL) were irradiated in a Biotage microwave for 40 min at 110° C. The reaction mixture was concentrated in vacuo, and the residue dissolved in DMSO, filtered and purified by prep HPLC (low pH) to afford a green solid (44 mg, 41%).

Workup

  1. concentrationThe reaction mixture was concentrated in vacuo
  2. dissolutionthe residue dissolved in DMSO
  3. filtrationfiltered
  4. custompurified by prep HPLC (low pH)

Sources & evidence

ORD record
ord-43c15ce14446465c8fac12439110515d
Source dataset
uspto-grants-2016_02
Patent number
US09249129B2

Reaction notes

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