1,8-Diazabicyclo(5.4.0)undec-7-ene → HCID 86674882, compound

HRID 716074Notes

Reaction equation

HRID 716074 reaction equation
C1CCN2C(=NCCC2)CC1.[NH2:12][C:13]1[N:21]=[C:20]2[C:16]([NH:17][CH:18]=[N:19]2)=[C:15]([Cl:22])[N:14]=1.[CH:23]([O:26][C:27]([O:36][CH:37]([CH3:39])[CH3:38])([P:32]([OH:35])([OH:34])=[O:33])[O:28][CH2:29][CH2:30]Cl)([CH3:25])[CH3:24]>CN(C=O)C>[NH2:12][C:13]1[N:21]=[C:20]2[C:16]([N:17]=[CH:18][N:19]2[CH2:30][CH2:29][O:28][C:27]([O:26][CH:23]([CH3:24])[CH3:25])([O:36][CH:37]([CH3:38])[CH3:39])[P:32]([OH:35])([OH:34])=[O:33])=[C:15]([Cl:22])[N:14]=1

Participants

5

Reactant 3

HCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 53603492-Amino-6-chloropurineHCID 86674883HCID 86674883, compound

Product 1

HCID 86674882HCID 86674882, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
80 °C

Procedure

In 120 ml DMF, 29.3 g of DBU, 32.45 g (0.191 mol) of 2-amino-6-chloropurine were added, stirred at 80° C. for 30 min, then 50 g (0.193 mol) of 2-(diisopropyloxy-phosphonomethoxy)-ethyl chloride was added, the reaction was performed at 100° C. for 8 h, cooled, distilled at a reduced pressure to remove DMF, added with water and ethyl acetate, layered, the water phase was extracted twice with ethyl acetate, the organic phases were combined, dried, separated by silica gel column chromatography, eluted with MeOH:CH2Cl2=1:30, yield 46 g of II1.

Workup

  1. waitthe reaction was performed at 100° C. for 8 h
  2. temperaturecooled
  3. distillationdistilled at a reduced pressure
  4. customto remove DMF
  5. additionadded with water and ethyl acetate
  6. extractionthe water phase was extracted twice with ethyl acetate
  7. customdried
  8. customseparated by silica gel column chromatography
  9. washeluted with MeOH

Sources & evidence

ORD record
ord-0fb8db0486cb4569a823968d57931bf4
Source dataset
uspto-grants-2015_11
Patent number
US09187507B2

Reaction notes

Loading…