Tetrabutylammonium Fluoride → 2-(4-Chloro-phenyl)-N-{5-[7-(3-hydroxymethyl-oxetan-3-yl)-7H-pyrrolo[2,3-d]pyrimidine-5-carbonyl]-pyridin-3-yl}-acetamide

HRID 82103Notes

Reaction equation

HRID 82103 reaction equation
C([SiH2][O:6][C:7](C)(C)[C:8]1([N:12]2[C:16]3[N:17]=[CH:18][N:19]=[CH:20][C:15]=3[C:14]([C:21]([C:23]3[CH:24]=[C:25]([NH:29][C:30](=[O:39])[CH2:31][C:32]4[CH:37]=[CH:36][C:35]([Cl:38])=[CH:34][CH:33]=4)[CH:26]=[N:27][CH:28]=3)=[O:22])=[CH:13]2)[CH2:11][O:10][CH2:9]1)(C)(C)C.[F-].C([N+](CCCC)(CCCC)CCCC)CCC>C1COCC1>[Cl:38][C:35]1[CH:36]=[CH:37][C:32]([CH2:31][C:30]([NH:29][C:25]2[CH:26]=[N:27][CH:28]=[C:23]([C:21]([C:14]3[C:15]4[CH:20]=[N:19][CH:18]=[N:17][C:16]=4[N:12]([C:8]4([CH2:7][OH:6])[CH2:11][O:10][CH2:9]4)[CH:13]=3)=[O:22])[CH:24]=2)=[O:39])=[CH:33][CH:34]=1

Participants

4

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 178455450HCID 178455450, compound

Product 1

HCID 708176612-(4-Chloro-phenyl)-N-{5-[7-(3-hydroxymethyl-oxetan-3-yl)-7H-pyrrolo[2,3-d]pyrimidine-5-carbonyl]-pyridin-3-yl}-acetamide

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

N-(5-{7-[3-(tert-Butyl-dimethyl-silanyloxymethyl)-oxetan-3-yl]-7H-pyrrolo[2,3-d]pyrimidine-5-carbonyl}-pyridin-3-yl)-2-(4-chloro-phenyl)-acetamide (Preparation 203 mg, 0.059 mmol) was dissolved in dry THF (0.5 mL) and tetrabutylammonium fluoride (0.065 mL of a 1M solution in THF, 0.065 mmol.) was added. The reaction was stirred for 30 min at room temperature. The mixture was partitioned between water and EtOAc. The layers were separated and the aqueous layer was extracted twice with EtOAc. The combined organic layers were concentrated and purified by preparative HPLC to give the title compound in quantitative yield 28 mg.

Workup

  1. addition) was added
  2. customThe mixture was partitioned between water and EtOAc
  3. customThe layers were separated
  4. extractionthe aqueous layer was extracted twice with EtOAc
  5. concentrationThe combined organic layers were concentrated
  6. custompurified by preparative HPLC

Sources & evidence

ORD record
ord-8a809d00eb364fd0bbaf1e0b0e3c48ca
Source dataset
uspto-grants-2014_09
Patent number
US08846698B2

Reaction notes

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