Potassium Carbonate → HCID 67050494, compound

HRID 2194805Notes

Reaction equation

HRID 2194805 reaction equation
[CH3:1][C:2]1[CH:3]=[C:4]([N:9]([C:13]2[NH:14][C:15](=[O:23])[NH:16][C:17](=[O:22])[C:18]=2[CH:19]([CH3:21])[CH3:20])[C:10](=[O:12])[CH3:11])[CH:5]=[C:6]([CH3:8])[CH:7]=1.ClC1N=C(Cl)[C:28]([CH:32](C)[CH3:33])=[C:27](Cl)N=1.C([O-])([O-])=O.[K+].[K+].[I-].[Li+].CS(C/C=C/C)(=O)=O>CN(C=O)C.CCOCC>[CH2:27]([N:14]1[C:13]([N:9]([C:4]2[CH:3]=[C:2]([CH3:1])[CH:7]=[C:6]([CH3:8])[CH:5]=2)[C:10](=[O:12])[CH3:11])=[C:18]([CH:19]([CH3:21])[CH3:20])[C:17](=[O:22])[NH:16][C:15]1=[O:23])[CH:28]=[CH:32][CH3:33]

Participants

8

Reactant 5

HCID 11430Potassium CarbonateHCID 66321Lithium iodideHCID 2490092,4,6-Trichloro-5-isopropylpyrimidineHCID 15270286HCID 15270286, compoundHCID 21303243HCID 21303243, compound

Product 1

HCID 67050494HCID 67050494, compoundYield 54%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 6228DimethylformamideSolvent

Procedure

To a stirred solution of N-(3,5-dimethyl-phenyl)-N-(5-isopropyl-2,6-dioxo-1,2,3,6-tetrahydro-pyrimidin-4-yl)-acetamide (106) (prepared similarly to compound 109 in Scheme 36, below, except that 2,4,6-trichloro-5-isopropyl-pyrimidine was used instead of 2,4,6-trichloro-5-ethyl-pyrimidine) (600 mg, 1.9 mmol) anhydrous powdered K2CO3 (262 mg, 1.9 mmol), and lithium iodide (254 mg, 1.9 mmol) in DMF (7 mL), was added 1-methanesulfonyl-trans-2-butene (269 μL, 2.28 mmol). After stirring for 13 hr., 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, ethyl acetate:hexane (1:1)) to afford 382 mg (54%) of a white solid. m.p. 103-105° C.; m/z (EI) 369(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, ethyl acetate:hexane (1:1))

Sources & evidence

ORD record
ord-2eb475d4b9bb477e91b1cb3e4a523619
Source dataset
uspto-grants-2012_12
Patent number
US08334295B2

Reaction notes

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