Potassium Carbonate → HCID 58203438, compound

HRID 2194771Notes

Reaction equation

HRID 2194771 reaction equation
[C:1]([C:3]1[CH:4]=[C:5]([CH:25]=[C:26]([CH3:28])[CH:27]=1)[C:6]([C:8]1[N:13]([CH2:14][CH2:15][O:16][C:17](=[O:19])[CH3:18])[C:12](=[O:20])[NH:11][C:10](=[O:21])[C:9]=1[CH:22]([CH3:24])[CH3:23])=[O:7])#[N:2].C(=O)([O-])[O-].[K+].[K+].Br[CH2:36][C:37]1[CH:42]=[CH:41][C:40]([O:43][CH3:44])=[CH:39][CH:38]=1.[I-].[Li+]>CN(C=O)C.C(OCC)(=O)C>[C:1]([C:3]1[CH:4]=[C:5]([CH:25]=[C:26]([CH3:28])[CH:27]=1)[C:6]([C:8]1[N:13]([CH2:14][CH2:15][O:16][C:17](=[O:19])[CH3:18])[C:12](=[O:20])[N:11]([CH2:36][C:37]2[CH:42]=[CH:41][C:40]([O:43][CH3:44])=[CH:39][CH:38]=2)[C:10](=[O:21])[C:9]=1[CH:22]([CH3:24])[CH3:23])=[O:7])#[N:2]

Participants

7

Reactant 4

HCID 11430Potassium CarbonateHCID 66321Lithium iodideHCID 1650214-Methoxybenzyl bromideHCID 25213227HCID 25213227, compound2×

Product 1

HCID 58203438HCID 58203438, compoundYield 53.4%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

Acetic acid 2-[6-(3-cyano-5-methyl-benzoyl)-5-isopropyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl]-ethyl ester (Compound 8) (126 mg, 0.328 mmol, 1.0 eq.) was dissolved in 1.5 mL of DMF. Potassium carbonate (45 mg, 1 eq.) was added and the reaction mixture was stirred at room temperature for 10 minutes. 1-Bromomethyl-4-methoxy-benzene (47 μL, 0.328 mmol, 1 eq.) and lithium iodide (44 mg, 1 eq.) were added. The reaction mixture was stirred at room temperature overnight. Ethyl acetate was added to the reaction mixture, followed by washing with brine. The organic layer was concentrated down and purified (silica gel, 0-80% EtOAC/hexane) to give a white powder (88 mg, 0.175 mmol, 53%). LC-MS shows 504.1 (M+1).

Workup

  1. stirringThe reaction mixture was stirred at room temperature overnight
  2. washby washing with brine
  3. concentrationThe organic layer was concentrated down
  4. custompurified (silica gel, 0-80% EtOAC/hexane)

Sources & evidence

ORD record
ord-7cfb63ff21f646ae96dc6b3c8082e363
Source dataset
uspto-grants-2012_12
Patent number
US08334295B2

Reaction notes

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