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

HRID 33359

反応式

HRID 33359 の反応式
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

参加物

6

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

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)

後処理

  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

出典と根拠

ORDレコード
ord-111d6fea9fff42cfb2b4ea6057a5ce78
出典データセット
uspto-grants-2008_09
特許番号
US07429595B2

関連ノート

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