5,6,7,8-Tetrahydro(1)benzothieno(2,3-D)pyrimidin-4(3H)-one → HCID 44232232、化合物

HRID 2189012

反応式

HRID 2189012 の反応式
[N:1]1[C:6]2[S:7][C:8]3[CH2:13][CH2:12][CH2:11][CH2:10][C:9]=3[C:5]=2[C:4](=[O:14])[NH:3][CH:2]=1.[F:15][C:16]1[CH:21]=[C:20]([F:22])[CH:19]=[CH:18][C:17]=1[C:23]1([CH2:26][N:27]2[CH:31]=[N:30][CH:29]=[N:28]2)[CH2:25][O:24]1.C[O-].[Na+]>C(O)(C)(C)C>[F:15][C:16]1[CH:21]=[C:20]([F:22])[CH:19]=[CH:18][C:17]=1[C:23]([OH:24])([CH2:26][N:27]1[CH:31]=[N:30][CH:29]=[N:28]1)[CH2:25][N:3]1[C:4](=[O:14])[C:5]2[C:9]3[CH2:10][CH2:11][CH2:12][CH2:13][C:8]=3[S:7][C:6]=2[N:1]=[CH:2]1

参加物

5

反応物 3

HCID 986145,6,7,8-Tetrahydro(1)benzothieno(2,3-D)pyrimidin-4(3H)-oneHCID 101309211-[2-(2,4-Difluorophenyl)-2,3-epoxypropyl]-1H-1,2,4-triazoleHCID 10942334Sodium Methoxide

生成物 1

HCID 44232232HCID 44232232、化合物収率 60%

試薬・触媒・溶媒 1

HCID 6386tert-Butanol溶媒

実験手順

5,6,7,8-Tetrahydrobenzothieno[2,3-d]pyrimidin-4(3H)-one of Formula (4-A09) (1.0 g, 4.8 mmole), 1[[2-(2,4-difluorophenyl)oxiranyl]methyl]-1H-1,2,4-triazole of the Formula (5) (1.38 g, 5.8 mmole) and sodium methoxide (0.31 g, 5.8 mmole), were taken in two neck round bottom flask under inert atmosphere, dry t-butanol (30 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 (20 ml) was added to the reaction mixture, the compound from the reaction mixture was extracted with ethyl acetate (3×20 ml), dried, concentrated and purified by column chromatography to obtain the pure 3-[2-(2,4-Difluorophenyl)-2-hydroxy-3-[1,2,4]triazol-1-yl-propyl]-5,6,7,8-tetrahydrobenzothieno[2,3-d]pyrimidin-4(3H)-one (1-A09) (1.29 gm, 60%). 1HNMR (CDCl3, 200 MHz): 1.74-1.96 (m, 4H), 2.71-2.81 (m, 2H), 2.90-3.02 (m, 2H), 4.18 (d, J=14 Hz, 1H), 4.55 (d, J=14 Hz, 1H), 4.70 (d, J=14 Hz, 1H), 4.77 (d, J=14 Hz, 1H), 6.29 (bs, 1H), 6.72-6.92 (m, 2H), 7.51-7.62 (m, 1H), 7.85 (s, 2H), 8.13 (s, 1H).

後処理

  1. additionwas added to the above reaction mixture
  2. temperatureunder reflux for 12 hours
  3. customt-Butanol was removed on rotavapor, water (20 ml)
  4. additionwas added to the reaction mixture
  5. extractionthe compound from the reaction mixture was extracted with ethyl acetate (3×20 ml)
  6. customdried
  7. concentrationconcentrated
  8. custompurified by column chromatography

出典と根拠

ORDレコード
ord-0c4cfc6ba28048f49ac269bc2d34a87b
出典データセット
uspto-grants-2012_12
特許番号
US08324227B2

関連ノート

読み込み中…