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Potassium Carbonate → HCID 54059613, compound

HRID 2194812
Notes
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Reaction equation

HRID 2194812 reaction equation
[CH3:1][C:2]1[CH:3]=[C:4]([CH:17]=[C:18]([CH3:20])[CH:19]=1)[O:5][C:6]1[NH:11][C:10](=[O:12])[NH:9][C:8](=[O:13])[C:7]=1[CH:14]([CH3:16])[CH3:15].C([O-])([O-])=O.[K+].[K+].[I-].[Li+].CS([CH2:33]/[CH:34]=[CH:35]/[CH3:36])(=O)=O>CN(C=O)C.CCOCC>[CH2:33]([N:11]1[C:6]([O:5][C:4]2[CH:3]=[C:2]([CH3:1])[CH:19]=[C:18]([CH3:20])[CH:17]=2)=[C:7]([CH:14]([CH3:16])[CH3:15])[C:8](=[O:13])[NH:9][C:10]1=[O:12])[CH:34]=[CH:35][CH3:36]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 4

HCID 11430Potassium CarbonateHCID 66321Lithium iodideHCID 15270286HCID 15270286, compoundHCID 222565785-Isopropyl-6-(3,5-dimethylphenoxy)-2,4-pyrimidinedione

Product 1

HCID 54059613HCID 54059613, compoundYield 75%

Reagents, catalysts & solvents 2

HCID 3283
Diethyl Ether
Solvent
HCID 6228DimethylformamideSolvent

Procedure

To a stirred solution of 6-(3,5-dimethyl-phenoxy)-5-isopropyl-1H-pyrimidine-2,4-dione (114) (prepared using the methods of WO9518109, herein incorporated by reference in its entirety for all purposes; 274 mg, 1 mmol) anhydrous powdered K2CO3 (138 mg, 1 mmol), and lithium iodide (134 mg, 1 mmol) in DMF (5 mL), was added 1-methanesulfonyl-trans-2-butene (141 μL, 1.2 mmol). After stirring for 15 hrs., the reaction mixture was diluted with ether, washed with water, dried with MgSO4, filtered, and evaporated in vacuo. The residue was purified by silica gel column chromatography (eluent, ether:dichloromethane:hexane (1:1:2)) to afford 247 mg (75%) of a white solid. m.p. 141-143° C.; 1H-NMR (200 MHz, CDCl3) δ1.13 (6H, d, J=7.0 Hz), 1.59 (3H, d, J=6.0 Hz), 2.29 (6H, s), 2.72 (1H, m), 4.20 (2H, d, J=5.5 Hz), 5.34-5.61 (2H, m), 6.51 (2H, s), 6.75 (1H, s), 9.00 (1H, s); m/z (EI) 328(M+).

Workup

  1. washwashed with water
  2. dry with materialdried with MgSO4
  3. filtrationfiltered
  4. customevaporated in vacuo
  5. customThe residue was purified by silica gel column chromatography (eluent, ether:dichloromethane:hexane (1:1:2))

Sources & evidence

ORD record
ord-c04cc140fd5346a49cb52799712e2a68
Source dataset
uspto-grants-2012_12
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08334295B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes