Potassium Carbonate → HCID 68648418, compound

HRID 1162573Notes

Reaction equation

HRID 1162573 reaction equation
[CH3:1][O:2][C:3](=[O:30])[C:4]1[CH:9]=[CH:8][CH:7]=[C:6]([CH2:10][N:11]([CH:25]2[CH2:29][CH2:28][CH2:27][CH2:26]2)[C:12]2[CH:17]=[CH:16][N:15]=[C:14]([C:18]3[CH:23]=[CH:22][C:21]([OH:24])=[CH:20][CH:19]=3)[N:13]=2)[CH:5]=1.Br[CH2:32][CH:33]1[CH2:38][CH2:37][CH2:36][CH2:35][CH2:34]1.C([O-])([O-])=O.[K+].[K+]>[Br-].C([N+](CCCC)(CCCC)CCCC)CCC.CC(C)=O>[CH3:1][O:2][C:3](=[O:30])[C:4]1[CH:9]=[CH:8][CH:7]=[C:6]([CH2:10][N:11]([C:12]2[CH:17]=[CH:16][N:15]=[C:14]([C:18]3[CH:23]=[CH:22][C:21]([O:24][CH2:32][CH:33]4[CH2:38][CH2:37][CH2:36][CH2:35][CH2:34]4)=[CH:20][CH:19]=3)[N:13]=2)[CH:25]2[CH2:29][CH2:28][CH2:27][CH2:26]2)[CH:5]=1

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 137636Cyclohexane, (bromomethyl)-HCID 136352438HCID 136352438, compound

Product 1

HCID 68648418HCID 68648418, compoundYield 77.2%

Reagents, catalysts & solvents 2

HCID 74236Tetrabutylammonium BromideCatalystHCID 180AcetoneSolvent

Conditions

Temperature
100 °C

Procedure

To an acetone (3 mL) solution of 3-({cyclopentyl-[2-(4-hydroxy-phenyl)-pyrimidin-4-yl]-amino}-methyl)-benzoic acid methyl ester (23 mg, 0.057 mmol) was added (bromomethyl)cyclohexane (11 mg, 0.063 mmol), K2CO3 (36 mg, 0.26 mmol) and tetrabutyammonium bromide (0.4 mg, 0.003 mmol). The resulting reaction mixture was heated in a CEM Exployer PLS™ microwave at 100° C. for 30 min. After cooling to room temperature the reaction mixture was filtered, and the residue was washed with acetone (4 mL). The solution was concentrated, and the crude solid was purified by silica gel chromatography eluting with hexanes/ethyl acetate 4:1 then 2:1 to yield 22 mg of 3-({[2-(4-cyclohexylmethoxy-phenyl)-pyrimidin-4-yl]-cyclopentyl-amino}-methyl)-benzoic acid methyl ester. LCMS m/z: 501 (M+1)+.

Workup

  1. customThe resulting reaction mixture
  2. temperatureAfter cooling to room temperature the reaction mixture
  3. filtrationwas filtered
  4. washthe residue was washed with acetone (4 mL)
  5. concentrationThe solution was concentrated
  6. customthe crude solid was purified by silica gel chromatography
  7. washeluting with hexanes/ethyl acetate 4:1

Sources & evidence

ORD record
ord-ac88df738c454d3990f630f5488cc446
Source dataset
uspto-grants-2010_10
Patent number
US07820704B2

Reaction notes

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