Tetrabutylammonium Fluoride → [5-(4-cyclopentyl-7H-pyrrolo[2,3-d]pyrimidin-5-ylmethyl)-pyridin-2-yl]-(6-trifluoromethyl-pyridin-3-ylmethyl)-amine

HRID 1692840Notes

Reaction equation

HRID 1692840 reaction equation
C1(S([N:10]2[C:14]3[N:15]=[CH:16][N:17]=[C:18]([CH:19]4[CH2:23][CH2:22][CH2:21][CH2:20]4)[C:13]=3[C:12]([CH2:24][C:25]3[CH:26]=[CH:27][C:28]([NH:31][CH2:32][C:33]4[CH:34]=[N:35][C:36]([C:39]([F:42])([F:41])[F:40])=[CH:37][CH:38]=4)=[N:29][CH:30]=3)=[CH:11]2)(=O)=O)C=CC=CC=1.[F-].C([N+](CCCC)(CCCC)CCCC)CCC>O1CCCC1>[CH:19]1([C:18]2[C:13]3[C:12]([CH2:24][C:25]4[CH:26]=[CH:27][C:28]([NH:31][CH2:32][C:33]5[CH:34]=[N:35][C:36]([C:39]([F:40])([F:42])[F:41])=[CH:37][CH:38]=5)=[N:29][CH:30]=4)=[CH:11][NH:10][C:14]=3[N:15]=[CH:16][N:17]=2)[CH2:23][CH2:22][CH2:21][CH2:20]1

Participants

4

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 57963061[5-(7-benzenesulfonyl-4-cyclopentyl-7H-pyrrolo[2,3-d]pyrimidin-5-ylmethyl)-pyridin-2-yl]-(6-trifluoromethyl-pyridin-3-ylmethyl)-amine

Product 1

HCID 57963212[5-(4-cyclopentyl-7H-pyrrolo[2,3-d]pyrimidin-5-ylmethyl)-pyridin-2-yl]-(6-trifluoromethyl-pyridin-3-ylmethyl)-amineYield 26%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To [5-(7-benzenesulfonyl-4-cyclopentyl-7H-pyrrolo[2,3-d]pyrimidin-5-ylmethyl)-pyridin-2-yl]-(6-trifluoromethyl-pyridin-3-ylmethyl)-amine (53, 0.010 g, 0.017 mmol) in 0.597 mL of tetrahydrofuran under nitrogen, tetra-n-butylammonium fluoride (0.0557 mL, 1.00 M in tetrahydrofuran, 0.0557 mmol) was added. The reaction was stirred for 3 hours, then quenched with water. The aqueous layer was separated and extracted with ethyl acetate. The organic layers were combined and washed with brine, dried over magnesium sulfate, filtered and the filtrate concentrated under vacuum. The resulting material was purified by silica gel column chromatography, eluting with 25% methanol in dichloromethane. Appropriate fractions were combined and solvents removed under vacuum to provide the desired compound (P-0104, 0.002 g). MS (ESI) [M+H+]+=453.1.

Workup

  1. customquenched with water
  2. customThe aqueous layer was separated
  3. extractionextracted with ethyl acetate
  4. washwashed with brine
  5. dry with materialdried over magnesium sulfate
  6. filtrationfiltered
  7. concentrationthe filtrate concentrated under vacuum
  8. customThe resulting material was purified by silica gel column chromatography
  9. washeluting with 25% methanol in dichloromethane
  10. customsolvents removed under vacuum

Sources & evidence

ORD record
ord-ba87c08ffcd649f588ca2ebe769331f7
Source dataset
uspto-grants-2012_04
Patent number
US08158636B2

Reaction notes

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