Phenylboronic Acid → HCID 86699281, compound

HRID 2278646Notes

Reaction equation

HRID 2278646 reaction equation
C[Si]([N-][Si](C)(C)C)(C)C.[Na+].[N:11]1([C:17]2[N:18]=[C:19]([CH2:24][C:25]([O:27][CH2:28][CH3:29])=[O:26])[NH:20][C:21](=[O:23])[CH:22]=2)[CH2:16][CH2:15][O:14][CH2:13][CH2:12]1.[C:30]1(B(O)O)[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1>C1(C)C=CC=CC=1.CN(C)C1C=CN=CC=1.C([O-])(=O)C.[Cu+2].C([O-])(=O)C>[N:11]1([C:17]2[N:18]=[C:19]([CH2:24][C:25]([O:27][CH2:28][CH3:29])=[O:26])[N:20]([C:30]3[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=3)[C:21](=[O:23])[CH:22]=2)[CH2:12][CH2:13][O:14][CH2:15][CH2:16]1

Participants

7

Reactant 3

HCID 66827Phenylboronic AcidHCID 2724254Sodium bis(trimethylsilyl)amideHCID 135905419Ethyl 2-[4-(morpholin-4-yl)-6-oxo-1,6-dihydropyrimidin-2-yl]acetate

Product 1

HCID 86699281HCID 86699281, compoundYield 5.1%

Reagents, catalysts & solvents 3

HCID 8895Cupric acetateCatalystHCID 142844-(Dimethylamino)pyridineCatalystHCID 1140TolueneSolvent2×

Conditions

Temperature
95 °C

Procedure

6.24 ml of 0.6 M sodium bis(trimethylsilyl)amide in toluene are added to a suspension of 1 g of ethyl [4-(morpholin-4-yl)-6-oxo-1,6-dihydropyrimidin-2-yl]acetate (obtained in step 1d of example 1d), 912 mg of phenylboronic acid, 680 mg of copper(11) acetate and 1.37 g of 4-dimethylaminopyridine in 12 ml of toluene. The reaction mixture is heated at 95° C. for 16 hours under a stream of dry air, and then filtered through celite. The filtrate is concentrated under reduced pressure and the residue is purified twice by silica column chromatography, elution being carried out with a mixture of dichloromethane and methanol (90/10, V/V) and then with a mixture of diisopropyl ether and methanol (90/10, V/V), so as to give 65 mg of ethyl (4-morpholin-4-yl-6-oxo-1-phenyl-1,6-dihydropyrimidin-2-yl)acetate in the form of a white solid, the characteristics of which are the following:

Workup

  1. filtrationfiltered through celite
  2. concentrationThe filtrate is concentrated under reduced pressure
  3. customthe residue is purified twice by silica column chromatography, elution
  4. additionbeing carried out with a mixture of dichloromethane and methanol (90/10, V/V)
  5. additionwith a mixture of diisopropyl ether and methanol (90/10, V/V)

Sources & evidence

ORD record
ord-82fd107132d54f8085b5e140d610dd93
Source dataset
uspto-grants-2015_09
Patent number
US09133168B2

Reaction notes

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