Cesium carbonate → {4-[4,6-Bis-(4-methoxy-phenyl)-pyrimidin-2-ylmethoxy]-2-methyl-phenoxy}-acetic acid methyl ester

HRID 19507Notes

Reaction equation

HRID 19507 reaction equation
[CH3:1][O:2][C:3](=[O:14])[CH2:4][O:5][C:6]1[CH:11]=[CH:10][C:9]([OH:12])=[CH:8][C:7]=1[CH3:13].C(=O)([O-])[O-].[Cs+].[Cs+].Br[CH2:22][C:23]1[N:28]=[C:27]([C:29]2[CH:34]=[CH:33][C:32]([O:35][CH3:36])=[CH:31][CH:30]=2)[CH:26]=[C:25]([C:37]2[CH:42]=[CH:41][C:40]([O:43][CH3:44])=[CH:39][CH:38]=2)[N:24]=1>C(#N)C>[CH3:1][O:2][C:3](=[O:14])[CH2:4][O:5][C:6]1[CH:11]=[CH:10][C:9]([O:12][CH2:22][C:23]2[N:24]=[C:25]([C:37]3[CH:38]=[CH:39][C:40]([O:43][CH3:44])=[CH:41][CH:42]=3)[CH:26]=[C:27]([C:29]3[CH:30]=[CH:31][C:32]([O:35][CH3:36])=[CH:33][CH:34]=3)[N:28]=2)=[CH:8][C:7]=1[CH3:13]

Participants

5

Reactant 3

HCID 10796Cesium carbonateHCID 23549552Methyl (4-hydroxy-2-methylphenoxy)acetateHCID 590076462-Bromomethyl-4,6-bis-(4-methoxy-phenyl)-pyrimidine

Product 1

HCID 59007643{4-[4,6-Bis-(4-methoxy-phenyl)-pyrimidin-2-ylmethoxy]-2-methyl-phenoxy}-acetic acid methyl ester

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

(4-Hydroxy-2-methyl-phenoxy)-acetic acid methyl ester 4 (0.13 g, 0.66 mmol) is dissolved in dry acetonitrile (3 mL). Cesium carbonate (0.40 g, 1.2 mmol) is added, followed by 32-bromomethyl-4,6-bis-(4-methoxy-phenyl)-pyrimidine 24 from Step C above. The mixture is stirred under nitrogen at room temperature for 18 hours. The resulting suspension is filtered, the solids are washed with more acetonitrile, and the resulting clear solution is concentrated to yield crude {4-[4,6-Bis-(4-methoxy-phenyl)-pyrimidin-2-ylmethoxy]-2-methyl-phenoxy}-acetic acid methyl ester 25 as an oil. MS calculated for C29H29N2O6 (M+H+) 500.19. found 500.1.

Workup

  1. filtrationThe resulting suspension is filtered
  2. washthe solids are washed with more acetonitrile
  3. concentrationthe resulting clear solution is concentrated

Sources & evidence

ORD record
ord-f230f2b516d34ba7baca831b87570b8b
Source dataset
uspto-grants-2010_06
Patent number
US07745445B2

Reaction notes

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