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

HRID 33359

Reaction equation

HRID 33359 reaction equation
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

Participants

6

Reactant 4

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

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)

Workup

  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

Sources & evidence

ORD record
ord-111d6fea9fff42cfb2b4ea6057a5ce78
Source dataset
uspto-grants-2008_09
Patent number
US07429595B2

Linked notes

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