Dimethylformamide → HCID 18925251, compound

HRID 2194813Notes

Reaction equation

HRID 2194813 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].[I-].[Li+].CS([CH2:27][C:28]#[CH:29])(=O)=O.[CH3:30]N(C=O)C>CCOCC>[CH2:27]([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])[C:28]#[C:29][CH3:30]

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 66321Lithium iodideHCID 142414643-(Methanesulfonyl)prop-1-yneHCID 222565785-Isopropyl-6-(3,5-dimethylphenoxy)-2,4-pyrimidinedione

Product 1

HCID 18925251HCID 18925251, compoundYield 84%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

To a stirred solution of 6-(3,5-dimethyl-phenoxy)-5-isopropyl-1H-pyrimidine-2,4-dione (114) (548 mg, 2 mmol) anhydrous powdered K2CO3 (276 mg, 2 mmol), and lithium iodide (268 mg, 2 mmol) in DMF (10 mL), was added 1-methanesulfonyl-2-propyne (247 μL, 2.1 mmol). After stirring for 17 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, ethyl acetate:hexane (1:2)) to afford 546 mg (84%) of a white solid. m.p. 158-160° C.; 1H-NMR (200 MHz, CDCl3) δ1.15 (6H, d, J=7.0 Hz), 1.69 (3H, t, J=2.2 Hz), 2.32 (6H, s), 2.80 (1H, m), 4.43 (2H, q, J=2.2 Hz), 6.60 (2H, s), 6.78 (1H, s), 8.55 (1H, s); m/z (EI) 326(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 (1:2))

Sources & evidence

ORD record
ord-8135664a9d0f4d31bb66ee7e2885916a
Source dataset
uspto-grants-2012_12
Patent number
US08334295B2

Reaction notes

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