HomeMCPWorkbenchSkills
HomeWorkbenchNotificationsMe
llms.txt · MCP GuidePrivacy Policy · Terms of Service · Supportv1.8.0
  1. Home
  2. /Reaction

Ethyl Acetate → 6-(2-Amino-6-chloro-pyrimidin-4-yloxy)-benzofuran-3-carboxylic acid methyl ester

HRID 556363
Notes
Print preview

Reaction equation

HRID 556363 reaction equation
[CH3:1][O:2][C:3]([C:5]1[C:9]2[CH:10]=[CH:11][C:12]([OH:14])=[CH:13][C:8]=2[O:7][CH:6]=1)=[O:4].[NH2:15][C:16]1[N:21]=[C:20](Cl)[CH:19]=[C:18]([Cl:23])[N:17]=1.[O-]P([O-])([O-])=O.[K+].[K+].[K+].CCOC(C)=O>CN1C(=O)CCC1.O>[CH3:1][O:2][C:3]([C:5]1[C:9]2[CH:10]=[CH:11][C:12]([O:14][C:20]3[CH:19]=[C:18]([Cl:23])[N:17]=[C:16]([NH2:15])[N:21]=3)=[CH:13][C:8]=2[O:7][CH:6]=1)=[O:4]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 4

HCID 8857Ethyl AcetateHCID 62657Potassium Phosphate, TribasicHCID 655222-Amino-4,6-dichloropyrimidineHCID 59577559Methyl 6-hydroxybenzofuran-3-carboxylate

Product 1

HCID 866266276-(2-Amino-6-chloro-pyrimidin-4-yloxy)-benzofuran-3-carboxylic acid methyl ester

Reagents, catalysts & solvents 2

HCID 962
Water
Solvent
HCID 13387N-methyl-2-pyrrolidoneSolvent

Conditions

Temperature
60 °C

Procedure

A mixture of 6.20 g (32.3 mMol) 6-hydroxy-benzofuran-3-carboxylic acid methyl ester, 8.5 g (51.8 mMol) 2-amino-4,6-dichloropyrimidine and 14.2 g (67 mMol) K3PO4 in 250 ml NMP is stirred for 3.5 h at 60° C. Then the mixture is poured into 1 l EtOAc and 1 l water, the aq. layer separated off and extracted 3 times with EtOAc. The organic phases are washed with water and brine and dried (Na2SO4). Then char coal is added, the mixture filtered and the filtrate concentrated. Trituration from ether gives the title compound: m.p.: 213-214° C. More product can be obtained from the filtrate by column chromatography (SiO2; hexane/EtOAc 2:1) as described in step 9.4.

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. additionThen char coal is added
  6. filtrationthe mixture filtered
  7. concentrationthe filtrate concentrated

Sources & evidence

ORD record
ord-0ed7dff4d2b341c096f5fab8b3b1ca5c
Source dataset
uspto-grants-2011_11
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08058276B2

Reaction notes

Loading…

On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes