Triphenylphosphine → 2,6-Dichloro-9-(tetrahydro-2H-pyran-4-ylmethyl)-9H-purine

HRID 1011012Notes

Reaction equation

HRID 1011012 reaction equation
[O:1]1[CH2:6][CH2:5][CH:4]([CH2:7]O)[CH2:3][CH2:2]1.[Cl:9][C:10]1[N:18]=[C:17]2[C:13]([NH:14][CH:15]=[N:16]2)=[C:12]([Cl:19])[N:11]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N(C(OC(C)C)=O)=NC(OC(C)C)=O>C1COCC1>[Cl:9][C:10]1[N:18]=[C:17]2[C:13]([N:14]=[CH:15][N:16]2[CH2:7][CH:4]2[CH2:5][CH2:6][O:1][CH2:2][CH2:3]2)=[C:12]([Cl:19])[N:11]=1

Participants

6

Reactant 4

HCID 11776TriphenylphosphineHCID 75555Diisopropyl diazene-1,2-dicarboxylateHCID 2773573(Oxan-4-yl)methanolHCID 53244122,6-Dichloropurine

Product 1

HCID 576997032,6-Dichloro-9-(tetrahydro-2H-pyran-4-ylmethyl)-9H-purine

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A mixture of tetrahydro-2H-pyran-4-ylmethanol (2.44 g) and 2,6-dichloropurine (1.97 g) was dissolved in dry THF (25 mL). To this solution was added triphenylphosphine (5.51 g), followed by diisopropyl azodicarboxylate (4.14 mL) added drop wise. The temperature of the reaction was kept below 43° C. (some cooling with a water bath was required). The reaction was stirred overnight at ambient temperature before being quenched with water (100 mL) and extracted into ethyl acetate (50 mL, twice). The separated and combined organic layer was then washed with water (100 mL). The organic layer was separated and then dried by passing through a hydrophobic frit before evaporation under reduced pressure to give pale yellow viscous oil. The material was partially purified by silica chromatography (ISCO) using 0-100% ethyl acetate: cyclohexane.

Workup

  1. additionadded drop wise
  2. customwas kept below 43° C.
  3. custombefore being quenched with water (100 mL)
  4. extractionextracted into ethyl acetate (50 mL
  5. customThe separated
  6. washwas then washed with water (100 mL)
  7. customThe organic layer was separated
  8. customdried
  9. customby passing through a hydrophobic frit before evaporation under reduced pressure
  10. customto give pale yellow viscous oil
  11. customThe material was partially purified by silica chromatography (ISCO)

Sources & evidence

ORD record
ord-15f69cd0069b4d91a93ac13ace2a53e4
Source dataset
uspto-grants-2011_07
Patent number
US07977344B2

Reaction notes

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