Sodium Carbonate → (4-{4-[2-(3-Fluorophenylamino)-pyrimidin-5-yl]-phenyl}-cyclohexyl)-acetic acid methyl ester

HRID 1404219Notes

Reaction equation

HRID 1404219 reaction equation
Br[C:2]1[CH:3]=[N:4][C:5]([NH:8][C:9]2[CH:14]=[CH:13][CH:12]=[C:11]([F:15])[CH:10]=2)=[N:6][CH:7]=1.[CH3:16][O:17][C:18](=[O:41])[CH2:19][CH:20]1[CH2:25][CH2:24][CH:23]([C:26]2[CH:31]=[CH:30][C:29](B3OC(C)(C)C(C)(C)O3)=[CH:28][CH:27]=2)[CH2:22][CH2:21]1.C(=O)([O-])[O-].[Na+].[Na+]>COCCOC>[CH3:16][O:17][C:18](=[O:41])[CH2:19][CH:20]1[CH2:21][CH2:22][CH:23]([C:26]2[CH:27]=[CH:28][C:29]([C:2]3[CH:3]=[N:4][C:5]([NH:8][C:9]4[CH:14]=[CH:13][CH:12]=[C:11]([F:15])[CH:10]=4)=[N:6][CH:7]=3)=[CH:30][CH:31]=2)[CH2:24][CH2:25]1

Participants

5

Reactant 3

HCID 10340Sodium CarbonateHCID 57992171Methyl 2-(trans-4-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)cyclohexyl)acetateHCID 638743875-bromo-N-(3-fluorophenyl)pyrimidin-2-amine

Product 1

HCID 66615836(4-{4-[2-(3-Fluorophenylamino)-pyrimidin-5-yl]-phenyl}-cyclohexyl)-acetic acid methyl ester

Reagents, catalysts & solvents 1

HCID 80711,2-DimethoxyethaneSolvent

Conditions

Temperature
125 °C

Procedure

The mixture of (5-bromopyrimidin-2-yl)-(3-fluorophenyl)-amine (75 mg, 0.28 mmol), {4-[4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-phenyl]-cyclohexyl}-acetic acid methyl ester (Patent WO2004 047755) (100 mg, 0.28 mmol), PdCl2dppf (12 mg, 0.014 mmol), sodium carbonate (2M solution, 0.35 mL) and DME (2 mL) is heated in a microwave at 125° C. for 15 Min. The reaction mixture is extracted with EtOAc, washed with NH4Cl solution. The organic phase is dried with MgSO4, filtered and it is used directly in the next step: (M+H)+ 420.3.

Workup

  1. extractionThe reaction mixture is extracted with EtOAc
  2. washwashed with NH4Cl solution
  3. dry with materialThe organic phase is dried with MgSO4
  4. filtrationfiltered

Sources & evidence

ORD record
ord-7117512a16144a29ab3b17f7c5458ab7
Source dataset
uspto-grants-2014_12
Patent number
US08912208B2

Reaction notes

Loading…