Ethyl Acetate → HCID 44230589, compound

HRID 2189013Notes

Reaction equation

HRID 2189013 reaction equation
[C:1]([O:4][CH2:5][CH2:6][CH2:7][C:8]1[S:17][C:11]2[N:12]=[CH:13][NH:14][C:15](=[O:16])[C:10]=2[CH:9]=1)(=[O:3])[CH3:2].[F:18][C:19]1[CH:24]=[C:23]([F:25])[CH:22]=[CH:21][C:20]=1[C:26]1([CH2:29][N:30]2[CH:34]=[N:33][CH:32]=[N:31]2)[CH2:28][O:27]1.C(OCC)(=O)C.C(=O)([O-])[O-].[K+].[K+]>[Br-].C([N+](CCCC)(CCCC)CCCC)CCC.O>[F:18][C:19]1[CH:24]=[C:23]([F:25])[CH:22]=[CH:21][C:20]=1[C:26]([OH:27])([CH2:29][N:30]1[CH:34]=[N:33][CH:32]=[N:31]1)[CH2:28][N:14]1[C:15](=[O:16])[C:10]2[CH:9]=[C:8]([CH2:7][CH2:6][CH2:5][O:4][C:1](=[O:3])[CH3:2])[S:17][C:11]=2[N:12]=[CH:13]1

Participants

7

Reactant 4

HCID 8857Ethyl AcetateHCID 11430Potassium CarbonateHCID 101309211-(2-(2,4-Difluorophenyl)-2,3-epoxypropyl)-1H-1,2,4-triazoleHCID 68514832HCID 68514832, compound

Product 1

HCID 44230589HCID 44230589, compoundYield 31%

Reagents, catalysts & solvents 2

HCID 74236Tetrabutylammonium BromideCatalystHCID 962WaterSolvent

Procedure

6-(3-Acetoxypropyl)-thieno[2,3-d]pyrimidin-4(3H)-one of Formula (4-A26) (0.5 g, 2 mmole) and 1[[2-(2,4-difluorophenyl)oxiranyl]methyl]-1H-1,2,4-triazole of the Formula (5) (0.47 g, 2 mmole) were taken in two neck round bottom flask under inert atmosphere, dry ethyl acetate (5 ml) was added followed by flame dried potassium carbonate (0.55 g, 4 mmole) and tetrabutylammonium bromide (0.76 g, 2.4 mmole) the mixture was stirred under reflux for 12 hours, Cooled, diluted with water (15 ml), extracted with ethyl acetate (3×10 ml), dried, concentrated and purified by column chromatography afforded the pure 3-[2-(2,4-difluorophenyl)-2-hydroxy-3-[1,2,4]triazol-1-yl-propyl]-6-(3-acetoxypropyl)-thieno[2,3-d]pyrimidin-4(3H)-one (1-A26) (0.3 gm, 31%). 1HNMR (CDCl3, 200 MHz): 1.96-2.10 (m, 2H), 2.06 (s, 3H), 2.92 (t, J=8 Hz, 2H), 4.11 (t, J=6 Hz, 2H), 4.27 (d, J=14 Hz, 1H), 4.60 (d, J=14 Hz, 1H), 4.73 (d, J=14 Hz, 1H), 4.85 (d, J=14 Hz, 1H), 6.74-6.92 (m, 2H), 7.10 (s, 1H), 7.45-7.59 (m, 1H), 7.91 (bs, 1H), 7.95 (s, 1H), 8.36 (bs, 1H).

Workup

  1. additionwas added
  2. temperatureunder reflux for 12 hours
  3. temperatureCooled
  4. extractionextracted with ethyl acetate (3×10 ml)
  5. customdried
  6. concentrationconcentrated
  7. custompurified by column chromatography

Sources & evidence

ORD record
ord-3832e9e335274980a3a9b5b9c2a7447a
Source dataset
uspto-grants-2012_12
Patent number
US08324227B2

Reaction notes

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