Potassium Carbonate → 2-{2-[5-Chloro-2-(benzyloxy)phenyl]cyclopent-1-enyl}pyrimidine-4-carboxylic Acid Ethyl Ester

HRID 1767211Notes

Reaction equation

HRID 1767211 reaction equation
[CH3:1][O:2][C:3]([C:5]1[CH:10]=[CH:9][N:8]=[C:7](Cl)[N:6]=1)=[O:4].[CH2:12]([O:19][C:20]1[CH:25]=[CH:24][C:23]([Cl:26])=[CH:22][C:21]=1[C:27]1[CH2:31][CH2:30][CH2:29][C:28]=1B(O)O)[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.[C:35](=O)([O-])[O-].[K+].[K+].C1(C)C=CC=CC=1.C(O)C>C(OCC)C.O.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[CH2:1]([O:2][C:3]([C:5]1[CH:10]=[CH:9][N:8]=[C:7]([C:28]2[CH2:29][CH2:30][CH2:31][C:27]=2[C:21]2[CH:22]=[C:23]([Cl:26])[CH:24]=[CH:25][C:20]=2[O:19][CH2:12][C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[N:6]=1)=[O:4])[CH3:35]

Participants

7

Reactant 4

HCID 11430Potassium CarbonateHCID 211129122-(2-Benzyloxy-5-chlorophenyl)cyclopentene-1-boronic AcidHCID 21863594Toluene ethanolHCID 43811076Methyl 2-chloropyrimidine-4-carboxylate

Product 1

HCID 588876512-{2-[5-Chloro-2-(benzyloxy)phenyl]cyclopent-1-enyl}pyrimidine-4-carboxylic Acid Ethyl EsterYield 38%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 21584184Diethylether waterSolvent

Procedure

A mixture of 2-chloropyrimidine-4-carboxylic acid methyl ester (114 mg, 0.66 mmol), 2-(2-benzyloxy-5-chlorophenyl)cyclopentene-1-boronic acid (209 mg, 0.66 mmol), potassium carbonate (729 mg, 5.28 mmol) and tetrakis(triphenylphosphine)palladium(0) (76 mg, 0.066 mmol) was stirred and heated in 1:1 toluene/ethanol (6 ml) at 90° C. under nitrogen for 2 hours. After cooling the mixture was diluted with diethyl ether/water and the organic phase dried (magnesium sulphate), evaporated to dryness and the residue purified by chromatography on silica (12% ethyl acetate in iso-hexane) to yield the title compound as a colourless gum (109 mg, 38%). LC/MS: Rt 3.8 [MH+] 435.3, 437.3.

Workup

  1. temperatureAfter cooling the mixture
  2. dry with materialthe organic phase dried (magnesium sulphate)
  3. customevaporated to dryness
  4. customthe residue purified by chromatography on silica (12% ethyl acetate in iso-hexane)

Sources & evidence

ORD record
ord-3dc3444999ce48b8a77bc17f9e4bb751
Source dataset
uspto-grants-2007_06
Patent number
US07232821B2

Reaction notes

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