Potassium Carbonate → [8-(2-Methyl-pyrimidin-5-yl)-6-oxo-oct-7-enyl]-carbamic acid tert-butyl ester

HRID 860093Notes

Reaction equation

HRID 860093 reaction equation
COP([CH2:7][C:8](=[O:22])[CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][NH:14][C:15]([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:16])(=O)OC.C(=O)([O-])[O-].[K+].[K+].[CH3:29][C:30]1[N:35]=[CH:34][C:33]([CH:36]=O)=[CH:32][N:31]=1>C1COCC1.O>[C:18]([O:17][C:15](=[O:16])[NH:14][CH2:13][CH2:12][CH2:11][CH2:10][CH2:9][C:8](=[O:22])[CH:7]=[CH:36][C:33]1[CH:32]=[N:31][C:30]([CH3:29])=[N:35][CH:34]=1)([CH3:19])([CH3:20])[CH3:21]

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 31609702-Methylpyrimidine-5-carbaldehydeHCID 20622500(7-tert-Butoxycarbonylamino-2-oxo-heptyl)-phosphonic acid dimethyl ester

Product 1

HCID 73687172[8-(2-Methyl-pyrimidin-5-yl)-6-oxo-oct-7-enyl]-carbamic acid tert-butyl esterYield 58.9%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

A solution of 24-2 (3.13 g, 9.28 mmol), potassium carbonate (1.75 g, 12.6 mmol), and 2-methyl-pyrimidine-5-carbaldehyde (1.04 g, 8.51 mmol) in THF (20 mL) was warmed to 40 ° C. for 5 h. The mixture was diluted with water and extracted four times with ether. The combined organics were washed with brine and dried (Na2SO4). Purification via silica chromatography (hexane/ethyl acetate) afforded the title compound 24-3 (1.67 g).

Workup

  1. extractionextracted four times with ether
  2. washThe combined organics were washed with brine
  3. dry with materialdried (Na2SO4)
  4. customPurification via silica chromatography (hexane/ethyl acetate)

Sources & evidence

ORD record
ord-388ddb6430bd4b3f88dcac35983164f8
Source dataset
uspto-grants-2006_12
Patent number
US07153862B2

Reaction notes

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