Ethyl Acetate → HCID 86626628, compound

HRID 556368Notes

Reaction equation

HRID 556368 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[C:7]2[CH:14]=[CH:13][C:12]([OH:15])=[CH:11][C:8]=2[S:9][CH:10]=1)=[O:5])[CH3:2].[NH2:16][C:17]1[N:22]=[C:21](Cl)[CH:20]=[C:19]([Cl:24])[N:18]=1.[O-]P([O-])([O-])=O.[K+].[K+].[K+].CCOC(C)=O>CN1C(=O)CCC1.O>[CH2:1]([O:3][C:4]([C:6]1[C:7]2[CH:14]=[CH:13][C:12]([O:15][C:21]3[CH:20]=[C:19]([Cl:24])[N:18]=[C:17]([NH2:16])[N:22]=3)=[CH:11][C:8]=2[S:9][CH:10]=1)=[O:5])[CH3:2]

Participants

7

Reactant 4

HCID 8857Ethyl AcetateHCID 62657Potassium Phosphate, TribasicHCID 655222-Amino-4,6-dichloropyrimidineHCID 66992863HCID 66992863, compound

Product 1

HCID 86626628HCID 86626628, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 13387N-methyl-2-pyrrolidoneSolvent

Conditions

Temperature
60 °C

Procedure

A mixture of 2.563 g (11.5 mMol) 6-hydroxy-benzo[b]thiophene-3-carboxylic acid ethyl ester, 3.06 g (18.5 mMol) 2-amino-4,6-dichloropyrimidine and 5.15 g (23 mMol) K3PO4 in 87 ml NMP is stirred for 1.5 h at 60° C. Then the mixture is poured into EtOAc and water, the aq. layer separated off and extracted 3 times with EtOAc. The organic phases are washed with water and brine, dried (Na2SO4) and concentrated. Trituration in ether and filtration gives the title compound: m.p.: 178-179° C.; TLC(hexane/EtOAc 2:1): Rf=0.27. More product can be obtained from the filtrate by column chromatography (SiO2; hexane/EtOAc 3:1).

Workup

  1. customthe aq. layer separated off
  2. extractionextracted 3 times with EtOAc
  3. washThe organic phases are washed with water and brine
  4. dry with materialdried (Na2SO4)
  5. concentrationconcentrated
  6. filtrationTrituration in ether and filtration

Sources & evidence

ORD record
ord-a5ad343716504a35a6da85593847ea1c
Source dataset
uspto-grants-2011_11
Patent number
US08058276B2

Reaction notes

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