Triphenylmethyl phosphonium bromide → 4-[1-(1-Cyclopentylbut-3-en-1-yl)-1H-pyrazol-4-yl]-7-[2-(trimethylsilyl)ethoxy]methyl-7H-pyrrolo[2,3-d]pyrimidine

HRID 45035Notes

Reaction equation

HRID 45035 reaction equation
CC(C)([O-])C.[K+].[Br-].C1([C:14]([PH3+])([C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)[C:15]2[CH:20]=CC=CC=2)C=CC=CC=1.C1(C([N:37]2[CH:41]=[C:40]([C:42]3[C:43]4[CH:50]=[CH:49][N:48]([CH2:51][O:52][CH2:53][CH2:54][Si:55]([CH3:58])([CH3:57])[CH3:56])[C:44]=4[N:45]=[CH:46][N:47]=3)[CH:39]=[N:38]2)CC=O)CCCC1>C1COCC1>[CH:26]1([CH:21]([N:37]2[CH:41]=[C:40]([C:42]3[C:43]4[CH:50]=[CH:49][N:48]([CH2:51][O:52][CH2:53][CH2:54][Si:55]([CH3:58])([CH3:57])[CH3:56])[C:44]=4[N:45]=[CH:46][N:47]=3)[CH:39]=[N:38]2)[CH2:14][CH:15]=[CH2:20])[CH2:25][CH2:24][CH2:23][CH2:22]1

Participants

5

Reactant 3

HCID 21951224Triphenylmethyl phosphonium bromideHCID 23665647Potassium tert-butoxideHCID 574780313-Cyclopentyl-3-[4-(7-[2-(trimethylsilyl)ethoxy]methyl-7H-pyrrolo[2,3-d]pyrimidin-4-yl)-1H-pyrazol-1-yl]propanal

Product 1

HCID 574780344-[1-(1-Cyclopentylbut-3-en-1-yl)-1H-pyrazol-4-yl]-7-[2-(trimethylsilyl)ethoxy]methyl-7H-pyrrolo[2,3-d]pyrimidineYield 44%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent3×

Procedure

To a solution of 1.0 M potassium tert-butoxide in THF (0.207 mL) in THF (2.0 mL) at 0° C. was added triphenylmethylphosphonium bromide (77.8 mg, 0.218 mmol). The resulting mixture was warmed to room temperature and allowed to stir for 30 minutes. A solution of 3-cyclopentyl-3-[4-(7-[2-(trimethylsilyl)ethoxy]methyl-7H-pyrrolo[2,3-d]pyrimidin-4-yl)-1H-pyrazol-1-yl]propanal (0.100 g, 0.228 mmol) in THF (2.0 mL) was added. After 30 minutes, the mixture was quenched by the addition of saturated ammonium chloride solution and the product was then extracted with ether. The ether extract was dried over sodium sulfate and the solvent was removed in vacuo. Flash column chromatography (eluting with a gradient of 0-40% ethyl acetate in hexanes) afforded the product (40 mg, 44%).

Workup

  1. waitAfter 30 minutes
  2. customthe mixture was quenched by the addition of saturated ammonium chloride solution
  3. extractionthe product was then extracted with ether
  4. extractionThe ether extract
  5. dry with materialwas dried over sodium sulfate
  6. customthe solvent was removed in vacuo
  7. washFlash column chromatography (eluting with a gradient of 0-40% ethyl acetate in hexanes)

Sources & evidence

ORD record
ord-b9f9e8a5a5654dcbac65a2fe22101814
Source dataset
uspto-grants-2013_09
Patent number
US08541425B2

Reaction notes

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