Ethanol → 3-fluoro-1-[4-(7H-pyrrolo[2,3-d]pyrimidin-4-yl)-1H-pyrazol-1-yl]cyclobutylacetonitrile

HRID 1966169Notes

Reaction equation

HRID 1966169 reaction equation
O[CH:2]1[CH2:5][C:4]([CH2:20][C:21]#[N:22])([N:6]2[CH:10]=[C:9]([C:11]3[C:12]4[CH:19]=[CH:18][NH:17][C:13]=4[N:14]=[CH:15][N:16]=3)[CH:8]=[N:7]2)[CH2:3]1.COCCN(CCOC)S(F)(F)[F:29].C(O)C>ClCCl>[F:29][CH:2]1[CH2:5][C:4]([CH2:20][C:21]#[N:22])([N:6]2[CH:10]=[C:9]([C:11]3[C:12]4[CH:19]=[CH:18][NH:17][C:13]=4[N:14]=[CH:15][N:16]=3)[CH:8]=[N:7]2)[CH2:3]1

Participants

5

Reactant 3

HCID 702EthanolHCID 2734690(Bis(2-methoxyethyl)amino)sulfur trifluorideHCID 442322253-hydroxy-1-[4-(7H-pyrrolo[2,3-d]pyrimidin-4-yl)-1H-pyrazol-1-yl]cyclobutylacetonitrile

Product 1

HCID 442322263-fluoro-1-[4-(7H-pyrrolo[2,3-d]pyrimidin-4-yl)-1H-pyrazol-1-yl]cyclobutylacetonitrile

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 3-hydroxy-1-[4-(7H-pyrrolo[2,3-d]pyrimidin-4-yl)-1H-pyrazol-1-yl]cyclobutylacetonitrile (0.01 g, 0.00003 mol) (a mixture of cis/trans isomers) in dichloromethane (3 mL), contained in a Teflon bottle equipped with a nitrogen inlet tube and stirring bar, was treated with 2-methoxy-N-(2-methoxyethyl)-N-(trifluoro-λ(4)-sulfanyl)ethanamine (0.03 mL, 0.0002 mol) at rt. Ethanol (0.002 mL, 0.00003 mol) was added, and the mixture was stirred at rt over weekend. The reaction was evaporated to dry and the residue was purified with prep. HPLC (pH=10) to give a mixture of two isomers. LCMS calculated for C15H14FN6(M+H)+: 297.1. Found: 297.3.

Workup

  1. customequipped with a nitrogen inlet tube
  2. stirringthe mixture was stirred at rt over weekend
  3. customThe reaction was evaporated
  4. customto dry
  5. customthe residue was purified with prep
  6. customHPLC (pH=10) to give
  7. additiona mixture of two isomers

Sources & evidence

ORD record
ord-f790264460144e2c8fc4a93f0fddaca2
Source dataset
uspto-grants-2013_04
Patent number
US08420629B2

Reaction notes

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