Potassium Carbonate → HCID 178512470, compound

HRID 643504Notes

Reaction equation

HRID 643504 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]([C:8]2[CH:13]=[CH:12][C:11]([NH:14][C:15]([NH2:17])=[NH:16])=[CH:10][CH:9]=2)[CH:5]=[CH:6][CH:7]=1.[Cl:18][C:19]1[N:24]=[C:23](Cl)[CH:22]=[CH:21][N:20]=1.C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C>[Cl:18][C:19]1[N:24]=[C:23]([O:1][C:2]2[CH:3]=[C:4]([C:8]3[CH:13]=[CH:12][C:11]([NH:14][C:15]([NH2:17])=[NH:16])=[CH:10][CH:9]=3)[CH:5]=[CH:6][CH:7]=2)[CH:22]=[CH:21][N:20]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 775312,4-DichloropyrimidineHCID 178512469HCID 178512469, compound

Product 1

HCID 178512470HCID 178512470, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of N-(3′-hydroxy-biphenyl-4-yl)guanidine (550 mg), 2,4-dichloropyrimidine (146 mg) and potassium carbonate (196 mg) in DMF (8 ml) is stirred at rt for 20 h. This mixture is purified by preparative HPLC (gradient of water, 0.1% TFA/acetonitrile, 0.1% TFA from 80/20 to 0/100 on Nucleosil 100-10 C18 column). The fractions containing product are basified with 1 N NaOH to pH 8, evaporated and dried under reduced pressure. The residue is stirred in ethanol, the solvent is evaporated and dried under reduced pressure to afford crude N-[3′-(2-chloro-pyrimidin-4-yloxy)biphenyl-4-yl]-guanidine.

Workup

  1. customThis mixture is purified by preparative HPLC (gradient of water, 0.1% TFA/acetonitrile, 0.1% TFA from 80/20 to 0/100 on Nucleosil 100-10 C18 column)
  2. additionThe fractions containing product
  3. customevaporated
  4. customdried under reduced pressure
  5. stirringThe residue is stirred in ethanol
  6. customthe solvent is evaporated
  7. customdried under reduced pressure

Sources & evidence

ORD record
ord-06023ae577c8481d878c3f16188bb63e
Source dataset
uspto-grants-2010_04
Patent number
US07700605B2

Reaction notes

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