1,8-Diazabicyclo(5.4.0)undec-7-ene → HCID 86600376, compound

HRID 1785447Notes

Reaction equation

HRID 1785447 reaction equation
O[CH2:2][C:3]1[CH:8]=[CH:7][C:6]([CH2:9][CH:10]([NH:12][C:13]2[N:18]=[C:17]([N:19]3[CH2:24][CH2:23][C:22](=[O:25])[N:21]4[CH2:26][CH:27]=[C:28]([C:30]5[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=5)[N:29]=[C:20]34)[CH:16]=[CH:15][N:14]=2)[CH3:11])=[CH:5][CH:4]=1.N12CCCN=C1CCCCC2.C1(P([N:61]=[N+:62]=[N-:63])(C2C=CC=CC=2)=O)C=CC=CC=1>O1CCCC1>[N:61]([CH2:2][C:3]1[CH:8]=[CH:7][C:6]([CH2:9][CH:10]([NH:12][C:13]2[N:18]=[C:17]([N:19]3[CH2:24][CH2:23][C:22](=[O:25])[N:21]4[CH2:26][CH:27]=[C:28]([C:30]5[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=5)[N:29]=[C:20]34)[CH:16]=[CH:15][N:14]=2)[CH3:11])=[CH:5][CH:4]=1)=[N+:62]=[N-:63]

Participants

5

Reactant 3

HCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 199401P,P-Diphenylphosphinic azideHCID 69066824HCID 69066824, compound

Product 1

HCID 86600376HCID 86600376, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

The mixture of 1-{2-[2-(4-hydroxymethyl-phenyl)-1-methyl-ethylamino]-pyrimidin-4-yl}-8-phenyl-1,2,3,6-tetrahydro -pyrimido[1,2-a]pyrimidin-4-one (0.11 g, 0.24 mmol) and 1,8-diaza-bicyclo[5.4.0]undec-7-ene (47 μL, 0.312 mmol) in tetrahydrofuran (5 mL) was brought to 0° C. followed by the addition of diphenylphosphoryl azide (68 μL, 0.312 mmol). The mixture was removed from the ice-bath and stirred at room temperature for 17 h. The mixture was concentrated and chromatographed on silica gel using 0-8% 2M NH3 MeOH/CH2Cl2to afford a white solid. M+1=494.

Workup

  1. customwas brought to 0° C.
  2. customThe mixture was removed from the ice-bath
  3. concentrationThe mixture was concentrated
  4. customchromatographed on silica gel using 0-8% 2M NH3 MeOH/CH2Cl2to
  5. customafford a white solid

Sources & evidence

ORD record
ord-520a25fcf6cc443b94c8b137ba59102e
Source dataset
uspto-grants-2009_03
Patent number
US07504403B2

Reaction notes

Loading…