Water → 4-(2-Butynyloxy)-6-(1-phenylvinyl)pyrimidine

HRID 1759932Notes

Reaction equation

HRID 1759932 reaction equation
[CH2:1]([O:5][C:6]1[N:11]=[CH:10][N:9]=[C:8]([C:12](O)([CH3:19])[C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[CH:7]=1)[C:2]#[C:3][CH3:4].FC1(F)N(C)CCN1C.O>C(#N)C>[N:9]1[CH:8]=[CH:7][CH:6]=[N:11][CH:10]=1.[CH2:1]([O:5][C:6]1[CH:7]=[C:8]([C:12]([C:13]2[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=2)=[CH2:19])[N:9]=[CH:10][N:11]=1)[C:2]#[C:3][CH3:4]

Participants

6

Reactant 3

HCID 962WaterHCID 27791112,2-Difluoro-1,3-dimethylimidazolidineHCID 225996786-(2-Butynyloxy)-4-(alpha-hydroxy-alpha-methylbenzyl)pyrimidine

Product 2

HCID 9260PyrimidineHCID 225998064-(2-Butynyloxy)-6-(1-phenylvinyl)pyrimidineYield 58.5%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent2×

Procedure

To a solution of 0.33 g of 6-(2-butynyloxy)-4-(α-hydroxy-α-methylbenzyl)pyrimidine in 4 ml of acetonitrile was added dropwise a solution of 0.2 g of 2,2-difluoro-1,3-dimethylimidazolidine in 2 ml of acetonitrile, followed by stirring at room temperature for 6 hours. The reaction mixture was then poured into water and extracted three times with ethyl acetate. The organic layers were combined and washed with a saturated aqueous sodium chloride solution, and the combined organic layer was dried over anhydrous magnesium sulfate and then concentrated. The residue was subjected to silica gel column chromatography to give 0.20 g of 4-(2-butynyloxy)-6-α-fluoro-α-methylbenzyl)pyrimidine (the present compound (154)) and 0.09 g of 4-(2-butynyloxy)-6-(1-phenylvinyl)pyrimidine (the present compound (155)).

Workup

  1. extractionextracted three times with ethyl acetate
  2. washwashed with a saturated aqueous sodium chloride solution
  3. dry with materialthe combined organic layer was dried over anhydrous magnesium sulfate
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-b3859c028bde4bc38c08ac868db6e65e
Source dataset
uspto-grants-2005_01
Patent number
US06838463B2

Reaction notes

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