2-(Benzenesulfonyl)-3-phenyloxaziridine → Ethyl 6-(2-ethoxy-1-hydroxy-2-oxoethyl)-7-iodo-5-methylpyrazolo[1,5-a]pyrimidine-2-carboxylate

HRID 1630306ノート

反応式

HRID 1630306 の反応式
C[Si]([N-][Si](C)(C)C)(C)C.[K+].C1C[O:14]CC1.[CH2:16]([O:18][C:19](=[O:37])[CH2:20][C:21]1[C:22]([CH3:36])=[N:23][C:24]2[N:25]([N:28]=[C:29]([C:31]([O:33][CH2:34][CH3:35])=[O:32])[CH:30]=2)[C:26]=1[I:27])[CH3:17].C1(C2ON2S(C2C=CC=CC=2)(=O)=O)C=CC=CC=1>C1COCC1>[CH2:16]([O:18][C:19](=[O:37])[CH:20]([C:21]1[C:22]([CH3:36])=[N:23][C:24]2[N:25]([N:28]=[C:29]([C:31]([O:33][CH2:34][CH3:35])=[O:32])[CH:30]=2)[C:26]=1[I:27])[OH:14])[CH3:17]

参加物

5

反応物 3

HCID 3204052-(Benzenesulfonyl)-3-phenyloxaziridineHCID 86624818Khmds thfHCID 86691585Ethyl 6-(2-ethoxy-2-oxoethyl)-7-iodo-5-methylpyrazolo[1,5-a]pyrimidine-2-carboxylate

生成物 1

HCID 86691586Ethyl 6-(2-ethoxy-1-hydroxy-2-oxoethyl)-7-iodo-5-methylpyrazolo[1,5-a]pyrimidine-2-carboxylate収率 62.2%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒3 回

反応条件

温度
-78 °C

実験手順

To a stirred solution of 0.9M KHMDS/THF (39.1 mL, 35.2 mmol) in THF (100 mL) at −78° C. was added a THF (50 mL) solution of ethyl 6-(2-ethoxy-2-oxoethyl)-7-iodo-5-methylpyrazolo[1,5-a]pyrimidine-2-carboxylate (11.3 g, 27.1 mmol) over 5 min. After 30 min, a THF (50 mL) solution of 3-phenyl-2-(phenylsulfonyl)-1,2-oxaziridine (9.20 g, 35.2 mmol) was added to the red reaction mixture and stirred for additional 30 min at −78° C. Then, the resulting orange reaction mixture was quenched with sat. NH4Cl (50 mL), diluted with EtOAc (200 mL), washed with water (100 mL), brine (100 mL), dried (Na2SO4), filtered and concentrated to give solid. This solid was triturated with small amount of ethyl acetate and solids were filtered, washed with hexanes and dried under high vac to afford ethyl 6-(2-ethoxy-1-hydroxy-2-oxoethyl)-7-iodo-5-methylpyrazolo[1,5-a]pyrimidine-2-carboxylate (7.3 g, 16.85 mmol, 62.2% yield) as light yellow solid. 1H NMR (500 MHz, CDCl3) δ: 7.33 (s, 1H), 5.75 (d, J=2.1 Hz, 1H), 4.52 (qd, J=7.1, 1.2 Hz, 2H), 4.37-4.30 (m, 2H), 3.57 (d, J=2.4 Hz, 1H), 2.63 (s, 3H), 1.48 (t, J=7.2 Hz, 3H), 1.27 (t, J=7.0 Hz, 3H). LCMS (M+H)=434.1.

後処理

  1. customThen, the resulting orange reaction mixture was quenched with sat. NH4Cl (50 mL)
  2. additiondiluted with EtOAc (200 mL)
  3. washwashed with water (100 mL), brine (100 mL)
  4. dry with materialdried (Na2SO4)
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customto give solid
  8. customThis solid was triturated with small amount of ethyl acetate and solids
  9. filtrationwere filtered
  10. washwashed with hexanes
  11. customdried under high vac

出典と根拠

ORDレコード
ord-b210ac9929b4461abb257683cdc617c9
出典データセット
uspto-grants-2014_07
特許番号
US08791108B2

反応ノート

読み込み中…