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Methanol → tert-butyl 3-{[1-(3-benzyl-4-oxo-6,7,8,9-tetrahydro-4H-pyrido[1,2-a]pyrimidin-2-yl)propyl]amino}propylcarbamate

HRID 1784477
ノート
印刷プレビュー

反応式

HRID 1784477 の反応式
CS(O[CH:6]([C:9]1[N:10]=[C:11]2[CH2:26][CH2:25][CH2:24][CH2:23][N:12]2[C:13](=[O:22])[C:14]=1[CH2:15][C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)[CH2:7][CH3:8])(=O)=O.[NH2:27][CH2:28][CH2:29][CH2:30][NH:31][C:32](=[O:38])[O:33][C:34]([CH3:37])([CH3:36])[CH3:35].[I-].[K+].CO>CN(C=O)C.C(Cl)Cl>[NH3:10].[CH2:15]([C:14]1[C:13](=[O:22])[N:12]2[CH2:23][CH2:24][CH2:25][CH2:26][C:11]2=[N:10][C:9]=1[CH:6]([NH:27][CH2:28][CH2:29][CH2:30][NH:31][C:32](=[O:38])[O:33][C:34]([CH3:36])([CH3:35])[CH3:37])[CH2:7][CH3:8])[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=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

8

反応物 4

HCID 887MethanolHCID 4875Potassium IodideHCID 2735700tert-Butyl (3-aminopropyl)carbamateHCID 575932061-(3-benzyl-4-oxo-6,7,8,9-tetrahydro-4H-pyrido[1,2-a]pyrimidin-2-yl)propyl methanesulfonate

生成物 2

HCID 222Ammonia収率 0.1%
HCID 57593203
tert-butyl 3-{[1-(3-benzyl-4-oxo-6,7,8,9-tetrahydro-4H-pyrido[1,2-a]pyrimidin-2-yl)propyl]amino}propylcarbamate
収率 28.6%

試薬・触媒・溶媒 2

HCID 6228Dimethylformamide溶媒HCID 6344Dichloromethane溶媒

反応条件

温度
60 °C

実験手順

A mixture of 0.106 g (0.28 mmol) of the product from Step 9 (25), 0.15 g (0.84 mmol) of tert-butyl 3-aminopropylcarbamate, and 0.005 g (0.03 mmol) of potassium iodide in 5 mL of DMF was stirred at 60° C. under nitrogen for 24 hours. The reaction was quenched with water, extracted with ethyl acetate (4×) and the combined organic layers were washed with saturated NaHCO3 and brine and dried over MgSO4. The solvent was removed in vacuo and the crude reaction mixture was subjected to flash chromatography on a 7 cm column. Elution with a gradient of 50% ethyl acetate in hexanes, 100% ethyl acetate, 3% methanol and 0.1% ammonia in DCM, and 10% methanol and 0.1% ammonia in DCM yielded 0.019 g (0.04 mmol, 15%) of tert-butyl 3-{[1-(3-benzyl-4-oxo-6,7,8,9-tetrahydro-4H-pyrido[1,2-a]pyrimidin-2-yl)propyl]amino}propylcarbamate (26) as a clear oil.

後処理

  1. customThe reaction was quenched with water
  2. extractionextracted with ethyl acetate (4×)
  3. washthe combined organic layers were washed with saturated NaHCO3 and brine
  4. dry with materialdried over MgSO4
  5. customThe solvent was removed in vacuo
  6. customthe crude reaction mixture
  7. washElution with a gradient of 50% ethyl acetate in hexanes, 100% ethyl acetate, 3% methanol and 0.1% ammonia in DCM

出典と根拠

ORDレコード
ord-42dac9e0cc2e438baefdc9be2c640253
出典データセット
uspto-grants-2009_03
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US07504405B2

反応ノート

読み込み中…

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