Lithium iodide → HCID 86732068, 화합물

HRID 1498806

반응식

HRID 1498806 반응식
[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

참가 물질

6

반응물 3

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

생성물 1

HCID 86732068HCID 86732068, 화합물

시약·촉매·용매 2

HCID 10197677chromium(II) dichloride촉매HCID 8028Tetrahydrofuran용매3회

실험 절차

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

후처리

  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

출처 및 근거

ORD 기록
ord-71619895d0c54f9893fb7a84fcd3cf86
출처 데이터셋
uspto-grants-2015_12
특허 번호
US09200001B2

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