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Trifluoroacetic acid → {6-[(6-Methoxy-pyridin-3-ylmethyl)-amino]-2-methyl-pyridin-3-yl}-(7H-pyrrolo[2,3-d]pyrimidin-5-yl)-methanone

HRID 1775193
ノート
印刷プレビュー

反応式

HRID 1775193 の反応式
C(OC(=O)[N:7]([C:17]1[CH:22]=[CH:21][C:20]([CH:23]([OH:43])[C:24]2[C:32]3[CH:31]=[N:30][CH:29]=[N:28][C:27]=3[N:26]([Si](C(C)C)(C(C)C)C(C)C)[CH:25]=2)=[C:19]([CH3:44])[N:18]=1)[CH2:8][C:9]1[CH:10]=[N:11][C:12]([O:15][CH3:16])=[CH:13][CH:14]=1)(C)(C)C.C([SiH](CC)CC)C.FC(F)(F)C(O)=O>ClCCCl>[CH3:16][O:15][C:12]1[N:11]=[CH:10][C:9]([CH2:8][NH:7][C:17]2[N:18]=[C:19]([CH3:44])[C:20]([C:23]([C:24]3[C:32]4[CH:31]=[N:30][CH:29]=[N:28][C:27]=4[NH:26][CH:25]=3)=[O:43])=[CH:21][CH:22]=2)=[CH:14][CH:13]=1
参加物反応条件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 6422Trifluoroacetic acidHCID 12052TriethylsilaneHCID 57963213{5-[hydroxy-(7-triisopropylsilanyl-7H-pyrrolo[2,3-d]pyrimidin-5-yl)-methyl]-6-methyl-pyridin-2-yl}-(6-methoxy-pyridin-3-ylmethyl)-carbamic acid tert-butyl ester

生成物 1

HCID 57963198{6-[(6-Methoxy-pyridin-3-ylmethyl)-amino]-2-methyl-pyridin-3-yl}-(7H-pyrrolo[2,3-d]pyrimidin-5-yl)-methanone収率 30.7%

試薬・触媒・溶媒 1

HCID 11
1,2-Dichloroethane
溶媒

反応条件

温度
70 °C

実験手順

To {5-[hydroxy-(7-triisopropylsilanyl-7H-pyrrolo[2,3-d]pyrimidin-5-yl)-methyl]-6-methyl-pyridin-2-yl}-(6-methoxy-pyridin-3-ylmethyl)-carbamic acid tert-butyl ester (75, 0.317 g, 0.501 mmol) dissolved in 15.0 mL of 1,2-dichloroethane, triethylsilane (1.00 mL, 6.26 mmol) was added, followed by trifluoroacetic acid (0.482 mL, 6.26 mmol). The reaction was stirred at 70° C. overnight, then concentrated under vacuum and combined with 1 N aqueous potassium carbonate and extracted with ethyl acetate. The organic layer was washed with brine, then dried with sodium sulfate, filtered and the filtrate adsorbed onto silica. This was purified by silica gel column chromatography eluting with 50-100% ethyl acetate in hexanes. Appropriate fractions were combined and the solvents removed under vacuum to provide the desired compound (P-0019, 57.5 mg). 1H NMR was consistent with the compound structure.

後処理

  1. concentrationconcentrated under vacuum
  2. extractionextracted with ethyl acetate
  3. washThe organic layer was washed with brine
  4. dry with materialdried with sodium sulfate
  5. filtrationfiltered
  6. customThis was purified by silica gel column chromatography
  7. washeluting with 50-100% ethyl acetate in hexanes
  8. customthe solvents removed under vacuum

出典と根拠

ORDレコード
ord-ee99e8b639b146c484dee71ad15a6b3a
出典データセット
uspto-grants-2016_02
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US09260437B2

反応ノート

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このページの内容参加物反応条件実験手順後処理出典と根拠反応ノート