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

HRID 869116노트

반응식

HRID 869116 반응식
[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

참가 물질

7

반응물 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

생성물 1

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

시약·촉매·용매 1

HCID 6342Acetonitrile용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-a77d5a4da886420bafe34033ce007b6b
출처 데이터셋
uspto-grants-2015_03
특허 번호
US08969360B2

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