(+-)-2-Butanol → HCID 21922929, compound

HRID 886816Notes

Reaction equation

HRID 886816 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.[CH3:12][CH:13](O)[CH2:14][CH3:15].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>O1CCCC1>[CH:13]([N:8]1[CH:7]=[N:6][C:5]2[C:9]1=[N:10][C:2]([Cl:1])=[N:3][C:4]=2[Cl:11])([CH2:14][CH3:15])[CH3:12]

Participants

5

Reactant 3

HCID 6568(+-)-2-ButanolHCID 11776TriphenylphosphineHCID 53244122,6-Dichloropurine

Product 1

HCID 21922929HCID 21922929, compoundYield 50%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

2,6-dichloropurine (5.3 mmol), 2-Butanol (9.01 mmol), triphenylphosphine (7.95 mmol) in 40 ml anhydrous tetrahydrofuran, to which was added drop-wise diisoproplyazidodicarboxylate (7.95 mmol) at room temperature over a period of 30 minutes. The reaction mixture was stirred at room temperature for 24 hrs. The reaction is 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 on the silica gel column (10-80% ethyl acetate in petroleum ether, gradient elution), to give the desired compound in a yield of 50%.

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 on the silica gel column (10-80% ethyl acetate in petroleum ether, gradient elution)

Sources & evidence

ORD record
ord-8a63171e41b24b4da9b10ce508a0948a
Source dataset
uspto-grants-2012_08
Patent number
US08247410B2

Reaction notes

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