Lithium iodide → HCID 86732068、化合物

HRID 1498806

反応式

HRID 1498806 の反応式
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:22]=[CH:23][C:24]=1[O:25][CH3:26])[CH2:6][C:7]1[N:11]([C:12]2[CH:17]=[C:16]([CH:18]=[CH2:19])[N:15]=[C:14]([CH3:20])[N:13]=2)[N:10]=[C:9]([CH3:21])[N:8]=1.Cl[CH:28](Cl)[B:29]1[O:33][C:32]([CH3:35])([CH3:34])[C:31]([CH3:37])([CH3:36])[O:30]1.[I-].[Li+]>O1CCCC1.[Cl-].[Cr+2].[Cl-]>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:22]=[CH:23][C:24]=1[O:25][CH3:26])[CH2:6][C:7]1[N:11]([C:12]2[CH:17]=[C:16]([CH:18]3[CH2:19][CH:28]3[B:29]3[O:33][C:32]([CH3:35])([CH3:34])[C:31]([CH3:37])([CH3:36])[O:30]3)[N:15]=[C:14]([CH3:20])[N:13]=2)[N:10]=[C:9]([CH3:21])[N:8]=1

参加物

6

反応物 3

HCID 66321Lithium iodideHCID 110420412-(dichloromethyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolaneHCID 71548429HCID 71548429、化合物

生成物 1

HCID 86732068HCID 86732068、化合物

試薬・触媒・溶媒 2

HCID 10197677chromium(II) dichloride触媒HCID 8028Tetrahydrofuran溶媒3 回

実験手順

To a stirring slurry of chromium(II) chloride (630 mg, 5.12 mmol, 8.0 eq.) in dry tetrahydrofuran (10 ml) under nitrogen at 23° C. was added n,n,n′,n′-tetramethylethylenediamine (0.768 ml, 5.12 mmol, 8.0 eq.). The resulting blue reaction mixture was allowed to stir for 20 min. To the reaction mixture was added a solution of 4-(5-(3,4-dimethoxybenzyl)-3-methyl-1H-1,2,4-triazol-1-yl)-2-methyl-6-vinylpyrimidine (3-1, 225 mg, 0.640 mmol, 1.0.eq.) in tetrahydrofuran (2 mL) followed by a solution of 2-(dichloromethyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (270 mg, 1.281 mmol, 2.0 eq.) and lithium iodide (343 mg, 2.56 mmol, 4.0 eq) in tetrahydrofuran (2 mL). The resulting greenish blue reaction mixture was allowed to stir for 72 h. The reaction mixture was filtered, concentrated, and partitioned between ethyl acetate (100 mL) and water (100 mL). The organic layer was separated, dried over sodium sulfate, filtered and concentrated to afford 4-(5-(3,4-dimethoxybenzyl)-3-methyl-1H-1,2,4-triazol-1-yl)-2-methyl-6-(2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)cyclopropyl)pyrimidine (3-2). The crude material was carried forward with no purification. LRMS m/z (M+H) 492.5 found, 492.3 required

後処理

  1. customThe resulting greenish blue reaction mixture
  2. stirringto stir for 72 h
  3. filtrationThe reaction mixture was filtered
  4. concentrationconcentrated
  5. custompartitioned between ethyl acetate (100 mL) and water (100 mL)
  6. customThe organic layer was separated
  7. dry with materialdried over sodium sulfate
  8. filtrationfiltered
  9. concentrationconcentrated

出典と根拠

ORDレコード
ord-71619895d0c54f9893fb7a84fcd3cf86
出典データセット
uspto-grants-2015_12
特許番号
US09200001B2

関連ノート

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