1,8-Diazabicyclo(5.4.0)undec-7-ene → HCID 178441817, compound

HRID 705124Notes

Reaction equation

HRID 705124 reaction equation
[CH2:1]([C:5]1[NH:6][C:7](=O)[C:8]2[NH:13][N:12]=[C:11]([I:14])[C:9]=2[N:10]=1)[CH2:2][CH2:3][CH3:4].[CH3:16][O:17][C:18]1[CH:23]=[C:22]([O:24][CH3:25])[CH:21]=[CH:20][C:19]=1[CH2:26][NH2:27].N1CCCN2CCCCCC=12.C1CN([P+](ON2N=NC3C2=CC=CC=3)(N2CCCC2)N2CCCC2)CC1.F[P-](F)(F)(F)(F)F>C(#N)C>[CH2:1]([C:5]1[N:6]=[C:7]([NH:27][CH2:26][C:19]2[CH:20]=[CH:21][C:22]([O:24][CH3:25])=[CH:23][C:18]=2[O:17][CH3:16])[C:8]2[NH:13][N:12]=[C:11]([I:14])[C:9]=2[N:10]=1)[CH2:2][CH2:3][CH3:4]

Participants

6

Reactant 4

HCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 5972502,4-DimethoxybenzylamineHCID 2724699PyBOPHCID 178441541HCID 178441541, compound

Product 1

HCID 178441817HCID 178441817, compoundYield 51%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A solution of 5-butyl-3-iodo-1H-pyrazolo[4,3-d]pyrimidin-7(6H)-one (50 g, 157 mmol), (2,4-dimethoxyphenyl)methanamine (60 g, 359 mmol) and 2,3,4,6,7,8,9,10-octahydropyrimido[1,2-a]azepine (47.9 g, 314 mmol) in acetonitrile (500 mL) was treated with ((1H-benzo[d][1,2,3]triazol-1-yl)oxy)tri(pyrrolidin-1-yl)phosphonium hexafluorophosphate(V) (100 g, 192 mmol) and stirred for 6 hours at room temperature under nitrogen. The resulting suspension was filtered to remove precipitate and the filtrate was evaporated. The residue was purified on a silica cartridge (1500 g) (applied in minimum DCM) eluted with 0-80% cyclohexane-EtOAc (12 column volumes). Product-containing fractions were part evaporated to give a heavy suspension that was filtered and the solid air-dried to give the title compound (37.5 g, 80 mmol) as a white powder.

Workup

  1. filtrationThe resulting suspension was filtered
  2. customto remove precipitate
  3. customthe filtrate was evaporated
  4. customThe residue was purified on a silica cartridge (1500 g) (applied in minimum DCM)
  5. washeluted with 0-80% cyclohexane-EtOAc (12 column volumes)
  6. customevaporated
  7. customto give a heavy suspension that
  8. filtrationwas filtered
  9. customthe solid air-dried

Sources & evidence

ORD record
ord-30142807c39349ce968218911e12595b
Source dataset
uspto-grants-2015_11
Patent number
US09173872B2

Reaction notes

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