1-(2-(2,4-Difluorophenyl)-2,3-epoxypropyl)-1H-1,2,4-triazole → HCID 44232102, compound

HRID 2189011Notes

Reaction equation

HRID 2189011 reaction equation
[CH2:1]([O:8][CH2:9][CH2:10][CH2:11][C:12]1[S:21][C:15]2[N:16]=[CH:17][NH:18][C:19](=[O:20])[C:14]=2[CH:13]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[F:22][C:23]1[CH:28]=[C:27]([F:29])[CH:26]=[CH:25][C:24]=1[C:30]1([CH2:33][N:34]2[CH:38]=[N:37][CH:36]=[N:35]2)[CH2:32][O:31]1.C[O-].[Na+]>C(O)(C)(C)C>[CH2:1]([O:8][CH2:9][CH2:10][CH2:11][C:12]1[S:21][C:15]2[N:16]=[CH:17][N:18]([CH2:32][C:30]([C:24]3[CH:25]=[CH:26][C:27]([F:29])=[CH:28][C:23]=3[F:22])([OH:31])[CH2:33][N:34]3[CH:38]=[N:37][CH:36]=[N:35]3)[C:19](=[O:20])[C:14]=2[CH:13]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 101309211-(2-(2,4-Difluorophenyl)-2,3-epoxypropyl)-1H-1,2,4-triazoleHCID 10942334Sodium MethoxideHCID 68511832HCID 68511832, compound

Product 1

HCID 44232102HCID 44232102, compoundYield 14%

Reagents, catalysts & solvents 1

HCID 6386tert-ButanolSolvent

Procedure

6-(3-Benzyloxypropyl)-thieno[2,3-d]pyrimidin-4(3H)-one of Formula (4-A02) (3.0 g, 0.01 mole), 1[[2-(2,4-difluorophenyl)oxiranyl]methyl]-1H-1,2,4-triazole of the Formula (5) (2.82 g, 0.012 mole) and sodium methoxide (0.65 g, 0.012 mole), were taken in two neck round bottom flask under inert atmosphere, dry t-butanol (70 ml) was added to the above reaction mixture and the mixture was stirred under reflux for 12 hours. t-Butanol was removed on rotavapor, water (50 ml) was added to the reaction mixture, the compound from the reaction mixture was extracted with ethyl acetate (3×50 ml), dried, concentrated and purified by column chromatography to obtain the pure 6-(3-benzyloxypropyl)-3-[2-(2,4-difluorophenyl)-2-hydroxy-3-[1,2,4]triazol-1-ylpropyl]-thieno[2,3-d]pyrimidin-4(3H)-one (1-A02) (0.8 gm, 14%). 1HNMR (CDCl3, 200 MHz):: 1.91-2.06 (m, 2H), 2.95 (t, J=6 Hz, 2H), 3.51 (t, J=6 Hz, 2H), 4.21 (d, J=14 Hz, 1H), 4.49 (s, 2H), 4.52 (d, J=14 Hz, 1H), 4.72 (d, J=14 Hz, 1H), 4.79 (d, J=14 Hz, 1H), 6.22 (s, 1H), 6.72-6.88 (m, 2H), 7.08 (s, 1H), 7.31 (bs, 5H), 7.49-7.62 (m, 1H), 7.83 (s, 1H), 7.91 (s, 1H), 8.09 (s, 1H).

Workup

  1. additionwas added to the above reaction mixture
  2. temperatureunder reflux for 12 hours
  3. customt-Butanol was removed on rotavapor, water (50 ml)
  4. additionwas added to the reaction mixture
  5. extractionthe compound from the reaction mixture was extracted with ethyl acetate (3×50 ml)
  6. customdried
  7. concentrationconcentrated
  8. custompurified by column chromatography

Sources & evidence

ORD record
ord-8b0a198d6a9648808048b284dc5e846c
Source dataset
uspto-grants-2012_12
Patent number
US08324227B2

Reaction notes

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