Isopropanol → 2,6-dichloro-9-(propan-2-yl)-9H-purine

HRID 33359

반응식

HRID 33359 반응식
CCOC(/N=N/C(OCC)=O)=O.[Cl:13][C:14]1[N:22]=[C:21]2[C:17]([NH:18][CH:19]=[N:20]2)=[C:16]([Cl:23])[N:15]=1.[C:24]1(P(C2C=CC=CC=2)C2C=CC=CC=2)[CH:29]=CC=C[CH:25]=1.C(O)(C)C>C1COCC1>[Cl:13][C:14]1[N:22]=[C:21]2[C:17]([N:18]=[CH:19][N:20]2[CH:24]([CH3:29])[CH3:25])=[C:16]([Cl:23])[N:15]=1

참가 물질

6

반응물 4

HCID 3776IsopropanolHCID 11776TriphenylphosphineHCID 53244122,6-DichloropurineHCID 5462977Diethyl azodicarboxylate

생성물 1

HCID 112184902,6-dichloro-9-(propan-2-yl)-9H-purine수율 49%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

Add DEAD (4.7 g, 27.09 mmol) slowly to a solution of 2,6-dichloropurine (1, 5 g, 26.5 mmol), triphenylphosphine (1 1.75 g, 44.5 mmol) and isopropyl alcohol (2b, 10 ml) in THF (100 ml), and stir at room temperature for 24 hours. Concentrate the reaction mixture, dissolve the residue in DCM (20 ml) and filter to remove the unwanted solids. Load the filtrate onto a 90 gram silica gel column (Biotage), and elute with DCM/acetone (95:5). Concentrate the desired fractions to give 3.0 grams of 2,6-dichloro-9-isopropyl-9H-purine (3b). 1H-NMR (CDCl3): δ 8.2(s, 1H), 4.95 (pentet, 1H), 1.63 (d, 6H)

후처리

  1. concentrationConcentrate the reaction mixture
  2. dissolutiondissolve the residue in DCM (20 ml)
  3. filtrationfilter
  4. customto remove the unwanted solids
  5. washLoad the filtrate onto a 90 gram silica gel column (Biotage), and elute with DCM/acetone (95:5)
  6. concentrationConcentrate the desired fractions

출처 및 근거

ORD 기록
ord-111d6fea9fff42cfb2b4ea6057a5ce78
출처 데이터셋
uspto-grants-2008_09
특허 번호
US07429595B2

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