Potassium Carbonate → HCID 86622894, compound

HRID 643499Notes

Reaction equation

HRID 643499 reaction equation
[C:1]([O:5][C:6](=[O:22])[NH:7][CH2:8][C:9]1[CH:14]=[CH:13][C:12]([C:15]2[CH:20]=[CH:19][CH:18]=[C:17]([OH:21])[CH:16]=2)=[CH:11][CH:10]=1)([CH3:4])([CH3:3])[CH3:2].[Cl:23][C:24]1[N:29]=[C:28](Cl)[CH:27]=[CH:26][N:25]=1.C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C>[C:1]([O:5][C:6](=[O:22])[NH:7][CH2:8][C:9]1[CH:14]=[CH:13][C:12]([C:15]2[CH:20]=[CH:19][CH:18]=[C:17]([O:21][C:26]3[CH:27]=[CH:28][N:29]=[C:24]([Cl:23])[N:25]=3)[CH:16]=2)=[CH:11][CH:10]=1)([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 775312,4-DichloropyrimidineHCID 67456175HCID 67456175, compound

Product 1

HCID 86622894HCID 86622894, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of (3′-hydroxy-biphenyl-4-ylmethyl)-carbamic acid tert-butyl ester (435 mg), 2,4-dichloropyrimidine (221 mg) and potassium carbonate (295 mg) in DMF (10 ml) is stirred at rt for 20 h. This mixture is quenched with brine and extracted twice with EtOAc. The combined organic phases are dried over sodium sulfate, the solvent is evaporated and the resulting crude product is purified on silica (90 g) with cyclohexane/EtOAc 80/20 to afford pure [3′-(2-chloro-pyrimidin-4-yloxy)-biphenyl-4-ylmethyl]-carbamic acid tert-butyl ester.

Workup

  1. customThis mixture is quenched with brine
  2. extractionextracted twice with EtOAc
  3. dry with materialThe combined organic phases are dried over sodium sulfate
  4. customthe solvent is evaporated
  5. customthe resulting crude product is purified on silica (90 g) with cyclohexane/EtOAc 80/20

Sources & evidence

ORD record
ord-502855607dd2439fa85b4c0c40e07be4
Source dataset
uspto-grants-2010_04
Patent number
US07700605B2

Reaction notes

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