Sulfur, trifluoro(N-methylmethanaminato)- → HCID 23505756, compound

HRID 1884346Notes

Reaction equation

HRID 1884346 reaction equation
[CH2:1]([N:5]([CH2:27][CH3:28])[C:6]1[C:7]2[C:15]([CH3:16])=[CH:14][N:13]([C:17]3[C:22]([CH3:23])=[CH:21][C:20]([CH2:24]O)=[CH:19][C:18]=3[CH3:26])[C:8]=2[N:9]=[C:10]([CH3:12])[N:11]=1)[CH2:2][CH2:3][CH3:4].CN(S(F)(F)[F:33])C>C(Cl)Cl>[CH2:1]([N:5]([CH2:27][CH3:28])[C:6]1[C:7]2[C:15]([CH3:16])=[CH:14][N:13]([C:17]3[C:22]([CH3:23])=[CH:21][C:20]([CH2:24][F:33])=[CH:19][C:18]=3[CH3:26])[C:8]=2[N:9]=[C:10]([CH3:12])[N:11]=1)[CH2:2][CH2:3][CH3:4]

Participants

4

Reactant 2

HCID 123203Sulfur, trifluoro(N-methylmethanaminato)-HCID 23505732HCID 23505732, compound

Product 1

HCID 23505756HCID 23505756, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of {4-[4-(butyl-ethyl-amino)-2,5-dimethyl-pyrrolo[2,3-d]pyrimidin-7-yl]-3,5-dimethylphenyl}-methanol (0.071 g, 0.186 mmol) in 2 ml anhydrous methylene chloride was cooled to −78° C. and treated with dimethylaminosulfur trifluoride (0.063g, 0.390 mmol) and stirred at room temperature for 1 hour. The mixture was quenched with water and extracted with chloroform. The organic layer was washed with brine, dried, and concentrated to give an oil which was purified through silica gel using 2% methanol/chloroform as eluent to give the title compound as an off-white solid, mp 163-165° C.

Workup

  1. customThe mixture was quenched with water
  2. extractionextracted with chloroform
  3. washThe organic layer was washed with brine
  4. customdried
  5. concentrationconcentrated
  6. customto give an oil which
  7. customwas purified through silica gel using 2% methanol/chloroform as eluent

Sources & evidence

ORD record
ord-cd398e5afb0e445e80dd7eb0f008f48b
Source dataset
uspto-grants-2004_07
Patent number
US06765008B1

Reaction notes

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