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Tetrahydrofuran → 4-{2-(2-Aminopyrimidin-5-yl)-9-isobutyl-6-[(3S)-3-methylmorpholin-4-yl]-9H-purin-8-yl}piperazine-1-carboaldehyde

HRID 1876627
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HRID 1876627 반응식
[O:1]1CCC[CH2:2]1.[CH2:6]([N:10]1[C:18]([N:19]2[CH2:24][CH2:23][NH:22][CH2:21][CH2:20]2)=[N:17][C:16]2[C:11]1=[N:12][C:13]([C:32]1[CH:33]=[N:34][C:35]([NH2:38])=[N:36][CH:37]=1)=[N:14][C:15]=2[N:25]1[CH2:30][CH2:29][O:28][CH2:27][C@@H:26]1[CH3:31])[CH:7]([CH3:9])[CH3:8].N1(C=O)C2C=CC=CC=2N=N1.[OH-].[Na+]>CCOCC.C(Cl)(Cl)Cl>[NH2:38][C:35]1[N:36]=[CH:37][C:32]([C:13]2[N:12]=[C:11]3[C:16]([N:17]=[C:18]([N:19]4[CH2:24][CH2:23][N:22]([CH:2]=[O:1])[CH2:21][CH2:20]4)[N:10]3[CH2:6][CH:7]([CH3:9])[CH3:8])=[C:15]([N:25]3[CH2:30][CH2:29][O:28][CH2:27][C@@H:26]3[CH3:31])[N:14]=2)=[CH:33][N:34]=1
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

7

반응물 4

HCID 8028TetrahydrofuranHCID 14798Sodium HydroxideHCID 5767401H-Benzotriazole-1-carboxaldehydeHCID 593335555-{9-Isobutyl-6-[(3S)-3-methylmorpholin-4-yl]-8-piperazin-1-yl-9H-purin-2-yl}pyrimidin-2-amine

생성물 1

HCID 593336504-{2-(2-Aminopyrimidin-5-yl)-9-isobutyl-6-[(3S)-3-methylmorpholin-4-yl]-9H-purin-8-yl}piperazine-1-carboaldehyde수율 79%

시약·촉매·용매 2

HCID 3283Diethyl Ether용매HCID 6212Chloroform용매

실험 절차

A tetrahydrofuran (3 ml) solution of 5-{9-isobutyl-6-[(3S)-3-methylmorpholin-4-yl]-8-piperazin-1-yl-9H-purin-2-yl}pyrimidin-2-amine (103 mg, 0.23 mmol) and 1H-benzotriazole-1-carboaldehyde (37 mg, 0.25 mmol) was stirred at room temperature for 16 hours. Chloroform and 2 N aqueous sodium hydroxide solution were added to the reaction mixture and the resulting mixture was extracted with chloroform. The organic layer was dried over anhydrous magnesium sulfate and, after filtration, the filtrate was concentrated under reduced pressure. The residue was purified by flash silica gel column chromatography (methylene chloride:methanol=95:5) to give a solid. Ether was added to the resulting solid and the solid was collected by filtration and dried to give the title compound (86 mg, 79%) as a powder.

후처리

  1. extractionthe resulting mixture was extracted with chloroform
  2. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  3. filtrationafter filtration
  4. concentrationthe filtrate was concentrated under reduced pressure
  5. customThe residue was purified by flash silica gel column chromatography (methylene chloride:methanol=95:5)
  6. customto give a solid
  7. filtrationthe solid was collected by filtration
  8. customdried

출처 및 근거

ORD 기록
ord-2eb6ef3adb4c46cd9d72e84b31213320
출처 데이터셋
uspto-grants-2012_11
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08309546B2

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