2-(Dimethylamino)ethanol → Allyl 2-amino-5-(2-(dimethylamino)ethoxy)pyrazolo[1,5-a]pyrimidine-3-carboxylate

HRID 869116ノート

反応式

HRID 869116 の反応式
[NH2:1][C:2]1[C:11]([C:12]([O:14][CH2:15][CH:16]=[CH2:17])=[O:13])=[C:5]2[NH:6][C:7](=[O:10])[CH:8]=[CH:9][N:4]2[N:3]=1.N1C[CH2:20][CH2:21][N:22]2[CH2:28]CCCC[C:23]=12.N1(O[P+](N2CCCC2)(N2CCCC2)N2CCCC2)C2C=CC=CC=2N=N1.CN(C)CCO.C(=O)([O-])[O-].[Cs+].[Cs+]>CC#N>[NH2:1][C:2]1[C:11]([C:12]([O:14][CH2:15][CH:16]=[CH2:17])=[O:13])=[C:5]2[N:6]=[C:7]([O:10][CH2:20][CH2:21][N:22]([CH3:28])[CH3:23])[CH:8]=[CH:9][N:4]2[N:3]=1

参加物

7

反応物 5

HCID 79022-(Dimethylamino)ethanolHCID 10796Cesium carbonateHCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 2724700Benzotriazol-1-yl-oxytripyrrolidinophosphoniumHCID 136629519allyl 2-amino-5-oxo-4H-pyrazolo[1,5-a]pyrimidine-3-carboxylate

生成物 1

HCID 90412007Allyl 2-amino-5-(2-(dimethylamino)ethoxy)pyrazolo[1,5-a]pyrimidine-3-carboxylate収率 35%

試薬・触媒・溶媒 1

HCID 6342Acetonitrile溶媒

実験手順

To a mixture of allyl 2-amino-5-oxo-4H-pyrazolo[1,5-a]pyrimidine-3-carboxylate (1 g, 4.270 mmol) in MeCN (15 mL) was added 2,3,4,6,7,8,9,10-octahydropyrimido[1,2-a]azepine (975.1 mg, 957.9 μL, 6.405 mmol) and benzotriazol-1-yloxy(tripyrrolidin-1-yl)phosphonium (Phosphorus Hexafluoride Ion) (2.666 g, 5.124 mmol). After 5 minutes, 2-dimethylaminoethanol (3.806 g, 4.291 mL, 42.70 mmol) and cesium carbonate (5 g) were added and the mixture was stirred at room temperature for 30 minutes, followed by heating to 50° C. for 30 minutes. After cooling to room temperature the mixture was filtered and the solid washed with acetonitrile. The combined filtrate was concentrated in vacuo to an orange oil and purified by column chromatography using 4% MeOH/DCM as eluent to provide 4b (yield 35%) LC-MS (M+H)+=306.2.

後処理

  1. temperatureby heating to 50° C. for 30 minutes
  2. temperatureAfter cooling to room temperature the mixture
  3. filtrationwas filtered
  4. washthe solid washed with acetonitrile
  5. concentrationThe combined filtrate was concentrated in vacuo to an orange oil
  6. custompurified by column chromatography

出典と根拠

ORDレコード
ord-a77d5a4da886420bafe34033ce007b6b
出典データセット
uspto-grants-2015_03
特許番号
US08969360B2

反応ノート

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