Potassium Carbonate → HCID 67050492, compound

HRID 2194775Notes

Reaction equation

HRID 2194775 reaction equation
[CH:1]([C:4]1[C:9](=[O:10])[NH:8][C:7](=[O:11])[NH:6][C:5]=1[C:12]([C:14]1[CH:15]=[C:16]([CH:19]=[C:20]([CH3:22])[CH:21]=1)[C:17]#[N:18])=[O:13])([CH3:3])[CH3:2].C(=O)([O-])[O-].[K+].[K+].[CH2:29]([O:31][C:32](=[O:37])[CH:33]=[CH:34][CH2:35]Br)[CH3:30].[I-].[Li+]>CN(C=O)C.C(OCC)(=O)C>[CH2:29]([O:31][C:32](=[O:37])[CH:33]=[CH:34][CH2:35][N:6]1[C:5]([C:12](=[O:13])[C:14]2[CH:21]=[C:20]([CH3:22])[CH:19]=[C:16]([C:17]#[N:18])[CH:15]=2)=[C:4]([CH:1]([CH3:3])[CH3:2])[C:9](=[O:10])[NH:8][C:7]1=[O:11])[CH3:30]

Participants

7

Reactant 4

HCID 11430Potassium CarbonateHCID 66321Lithium iodideHCID 98102Ethyl 4-bromocrotonateHCID 468803773-(5-Isopropyl-2,6-dioxo-1,2,3,6-tetrahydro-pyrimidine-4-carbonyl)-5-methyl-benzonitrile2×

Product 1

HCID 67050492HCID 67050492, compoundYield 68%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

3-(5-Isopropyl-2,6-dioxo-1,2,3,6-tetrahydro-pyrimidine-4-carbonyl)-5-methyl-benzonitrile (Compound 1) (412 mg, 1.386 mmol, 1.0 eq.) was dissolved in 8 mL DMF. Potassium carbonate (191 mg, 1 eq.) was added and the reaction mixture was stirred at room temperature for 10 minutes. 4-Bromo-but-2-enoic acid ethyl ester (0.24 mL, 1 eq.) and lithium iodide (186 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 light yellow foam (384 mg, 68%). LC-MS shows 410.4 (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-660178e504e54db4a556108a7cdab181
Source dataset
uspto-grants-2012_12
Patent number
US08334295B2

Reaction notes

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