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

HRID 405862Notes

Reaction equation

HRID 405862 reaction equation
[Cl:1][C:2]1[N:10]=[C:9]2[C:5]([NH:6][CH:7]=[N:8]2)=[C:4]([Cl:11])[N:3]=1.[CH:12](O)([CH3:14])[CH3:13].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>O1CCCC1>[Cl:1][C:2]1[N:10]=[C:9]2[C:5]([N:6]=[CH:7][N:8]2[CH:12]([CH3:14])[CH3:13])=[C:4]([Cl:11])[N:3]=1

Participants

5

Reactant 3

HCID 3776IsopropanolHCID 11776TriphenylphosphineHCID 53244122,6-Dichloropurine

Product 1

HCID 112184902,6-dichloro-9-(propan-2-yl)-9H-purineYield 77%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

2,6-Dichloropurine (2 mmol), isopropanol (8 mmol) and triphenylphosphine (4 mmol) were taken up in 40 ml anhydrous tetrahydrofuran and diisoproplyazidodicarboxylate (4 mmol) was added drop wise at room temperature over a period of 30 min. The reaction mixture was then stirred at room temperature for a further 24 h. The reaction was periodically monitored by TLC or LC-MS. The reaction mixture was poured in to a beaker containing ice-cold water. Extraction of the aqueous layer, using 3×100 ml portions of ethyl acetate, afforded the crude product. This was purified by chromatography on a silica gel column (10-80% ethyl acetate in petroleum ether, gradient elution), to give 2,6-dichloro-9-isopropyl-9H-purine in a yield of 77%.

Workup

  1. additionThe reaction mixture was poured in to a beaker
  2. additioncontaining ice-cold water
  3. extractionExtraction of the aqueous layer
  4. customafforded the crude product
  5. customThis was purified by chromatography on a silica gel column (10-80% ethyl acetate in petroleum ether, gradient elution)

Sources & evidence

ORD record
ord-593719d8329c4973aa0985ea84afa8dd
Source dataset
uspto-grants-2014_06
Patent number
US08754080B2

Reaction notes

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