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Potassium Carbonate → (6-methoxy-pyridin-3-ylmethyl)-[5-(7H-pyrrolo[2,3-d]pyrimidine-5-carbonyl)-pyridin-2-yl]carbamic acid tert-butyl ester

HRID 1692855
ノート
印刷プレビュー

反応式

HRID 1692855 の反応式
[C:1]([O:5][C:6](=[O:34])[N:7]([C:17]1[CH:22]=[CH:21][C:20]([CH:23]([OH:33])[C:24]2[C:32]3[CH:31]=[N:30][CH:29]=[N:28][C:27]=3[NH:26][CH:25]=2)=[CH:19][N:18]=1)[CH2:8][C:9]1[CH:10]=[N:11][C:12]([O:15][CH3:16])=[CH:13][CH:14]=1)([CH3:4])([CH3:3])[CH3:2].CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C=CC=CC1=2)=O.C(=O)([O-])[O-].[K+].[K+]>ClCCl>[C:1]([O:5][C:6](=[O:34])[N:7]([CH2:8][C:9]1[CH:10]=[N:11][C:12]([O:15][CH3:16])=[CH:13][CH:14]=1)[C:17]1[CH:22]=[CH:21][C:20]([C:23]([C:24]2[C:32]3[CH:31]=[N:30][CH:29]=[N:28][C:27]=3[NH:26][CH:25]=2)=[O:33])=[CH:19][N:18]=1)([CH3:4])([CH3:3])[CH3:2]
参加物実験手順後処理出典と根拠反応ノート

参加物

5

反応物 3

HCID 11430Potassium CarbonateHCID 159087TriacetoxyperiodinaneHCID 57963192{5-[hydroxy-(7H-pyrrolo[2,3-d]pyrimidin-5-yl)-methyl]-pyridin-2-yl}-(6-methoxy-pyridin-3-ylmethyl)-carbamic acid tert-butyl ester

生成物 1

HCID 57963060(6-methoxy-pyridin-3-ylmethyl)-[5-(7H-pyrrolo[2,3-d]pyrimidine-5-carbonyl)-pyridin-2-yl]carbamic acid tert-butyl ester収率 35%

試薬・触媒・溶媒 1

HCID 6344
Dichloromethane
溶媒

実験手順

To {5-[hydroxy-(7H-pyrrolo[2,3-d]pyrimidin-5-yl)-methyl]-pyridin-2-yl}-(6-methoxy-pyridin-3-ylmethyl)-carbamic acid tert-butyl ester (72, 0.189 g, 0.409 mmol) in 4.0 mL of dichloromethane, Dess-Martin periodinane (0.208 g, 0.490 mmol) was added. The reaction was stirred at room temperature for 1 hour, then poured into aqueous potassium carbonate and extracted with ethyl acetate. The organic layer was dried over sodium sulfate, filtered and the filtrate concentrated under vacuum. The resulting material was purified by silica gel column chromatography, eluting with methanol and dichloromethane. Appropriate fractions were combined and the solvents removed under vacuum to provide the desired compound (73, 66 mg). 1H NMR was consistent with the compound structure.

後処理

  1. extractionextracted with ethyl acetate
  2. dry with materialThe organic layer was dried over sodium sulfate
  3. filtrationfiltered
  4. concentrationthe filtrate concentrated under vacuum
  5. customThe resulting material was purified by silica gel column chromatography
  6. washeluting with methanol and dichloromethane
  7. customthe solvents removed under vacuum

出典と根拠

ORDレコード
ord-2cf18d440b4f4f0ab2b7848d4bbc195c
出典データセット
uspto-grants-2012_04
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08158636B2

反応ノート

読み込み中…

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