1,8-Diazabicyclo(5.4.0)undec-7-ene → HCID 57478051, compound

HRID 1962824Notes

Reaction equation

HRID 1962824 reaction equation
[C:1](/[CH:3]=[CH:4]/[CH:5]1[CH2:9][CH2:8][N:7]([C:10]([O:12][CH2:13][C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)=[O:11])[CH2:6]1)#[N:2].C(/C=C\C1CCN(C(OCC2C=CC=CC=2)=O)C1)#N.C1CCN2C(=NCCC2)CC1.[NH:50]1[CH:54]=[C:53]([C:55]2[C:56]3[CH:63]=[CH:62][N:61]([CH2:64][O:65][CH2:66][CH2:67][Si:68]([CH3:71])([CH3:70])[CH3:69])[C:57]=3[N:58]=[CH:59][N:60]=2)[CH:52]=[N:51]1>C(#N)C>[C:1]([CH2:3][CH:4]([CH:5]1[CH2:9][CH2:8][N:7]([C:10]([O:12][CH2:13][C:14]2[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=2)=[O:11])[CH2:6]1)[N:50]1[CH:54]=[C:53]([C:55]2[C:56]3[CH:63]=[CH:62][N:61]([CH2:64][O:65][CH2:66][CH2:67][Si:68]([CH3:71])([CH3:70])[CH3:69])[C:57]=3[N:58]=[CH:59][N:60]=2)[CH:52]=[N:51]1)#[N:2]

Participants

6

Reactant 4

HCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 426313464-(1H-Pyrazol-4-yl)-7-(2-(trimethylsilyl)ethoxy)methyl-7 H-pyrrolo(2,3-d)-pyrimidineHCID 57478050HCID 57478050, compoundHCID 66597822HCID 66597822, compound

Product 1

HCID 57478051HCID 57478051, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a mixture of benzyl 3-[(E)-2-cyanovinyl]pyrrolidine-1-carboxylate and benzyl 3-[(Z)-2-cyanovinyl]pyrrolidine-1-carboxylate (241 mg, 0.940 mmol) and DBU (234 μL, 1.57 mmol) in ACN (13 mL) was added 4-(1H-pyrazol-4-yl)-7-[2-(trimethylsilyl)ethoxy]methyl-7H-pyrrolo[2,3-d]pyrimidine (250 mg, 0.78 mmol). The mixture was stirred at ambient temperature for 3 hours. The solvent was removed in vacuo. The resulting residue was dissolved in ethyl acetate, and the organic layer was washed sequentially with 1N HCl, water, saturated NaHCO3, and brine. The washed solution was dried over sodium sulfate and the solvent was removed in vacuo. Purification via flash column chromatography (eluting with a gradient of 0-100% [5% MeOH/DCM] in hexanes) afforded the product as a mixture of diastereomers (400 mg, 89%).

Workup

  1. customThe solvent was removed in vacuo
  2. dissolutionThe resulting residue was dissolved in ethyl acetate
  3. washthe organic layer was washed sequentially with 1N HCl, water, saturated NaHCO3, and brine
  4. dry with materialThe washed solution was dried over sodium sulfate
  5. customthe solvent was removed in vacuo
  6. customPurification via flash column chromatography (
  7. washeluting with a gradient of 0-100% [5% MeOH/DCM] in hexanes)
  8. customafforded the product
  9. additionas a mixture of diastereomers (400 mg, 89%)

Sources & evidence

ORD record
ord-b09323f4a5e84cd68ed4639f40768d9d
Source dataset
uspto-grants-2013_04
Patent number
US08415362B2

Reaction notes

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