1,8-Diazabicyclo(5.4.0)undec-7-ene → HCID 66597812, compound

HRID 1962814Notes

Reaction equation

HRID 1962814 reaction equation
[NH:1]1[CH:5]=[C:4]([C:6]2[C:7]3[CH:14]=[CH:13][N:12]([CH2:15][O:16][CH2:17][CH2:18][Si:19]([CH3:22])([CH3:21])[CH3:20])[C:8]=3[N:9]=[CH:10][N:11]=2)[CH:3]=[N:2]1.[C:23](/[CH:25]=[CH:26]/[C:27]1([C:30]#[N:31])[CH2:29][CH2:28]1)#[N:24].C1CCN2C(=NCCC2)CC1>C(#N)C>[C:23]([CH2:25][CH:26]([C:27]1([C:30]#[N:31])[CH2:29][CH2:28]1)[N:1]1[CH:5]=[C:4]([C:6]2[C:7]3[CH:14]=[CH:13][N:12]([CH2:15][O:16][CH2:17][CH2:18][Si:19]([CH3:22])([CH3:21])[CH3:20])[C:8]=3[N:9]=[CH:10][N:11]=2)[CH:3]=[N:2]1)#[N:24]

Participants

5

Reactant 3

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 574780401-[(E)-2-Cyanovinyl]cyclopropanecarbonitrile

Product 1

HCID 66597812HCID 66597812, compoundYield 59.5%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a solution of 4-(1H-pyrazol-4-yl)-7-[2-(trimethylsilyl)ethoxy]methyl-7H-pyrrolo[2,3-d]-pyrimidine (61.4 mg, 0.195 mmol) and 1-[(E)-2-cyanovinyl]cyclopropanecarbonitrile (23 mg, 0.19 mmol) in ACN (2 mL) was added DBU (58 μL, 0.39 mmol) and the resulting mixture was stirred for 16 hours. The ACN was evaporated, and the residue was dissolved in ethyl acetate. This solution was washed with 1.0 N HCl, water, and brine, and dried over sodium sulfate, and the solvent removed in vacuo. Flash column chromatography (eluting with a gradient from 0-80% ethyl acetate in hexanes) afforded the product (49 mg, 58%).

Workup

  1. customThe ACN was evaporated
  2. dissolutionthe residue was dissolved in ethyl acetate
  3. washThis solution was washed with 1.0 N HCl, water, and brine
  4. dry with materialdried over sodium sulfate
  5. customthe solvent removed in vacuo
  6. washFlash column chromatography (eluting with a gradient from 0-80% ethyl acetate in hexanes)

Sources & evidence

ORD record
ord-79c852c2e235418c8c92198543c18b38
Source dataset
uspto-grants-2013_04
Patent number
US08415362B2

Reaction notes

Loading…