1-Butanol → HCID 178509243, compound

HRID 1818731Notes

Reaction equation

HRID 1818731 reaction equation
C(OC([NH:8][NH:9][C:10]1[C:15]([C:16]#[N:17])=[CH:14][N:13]=[C:12]([O:18][C:19]2[CH:24]=[CH:23][C:22]([F:25])=[CH:21][C:20]=2[F:26])[N:11]=1)=O)(C)(C)C.FC(F)(F)C(O)=O.C(O)CCC.C(N(CC)CC)C>ClCCl>[F:26][C:20]1[CH:21]=[C:22]([F:25])[CH:23]=[CH:24][C:19]=1[O:18][C:12]1[N:11]=[C:10]2[NH:9][N:8]=[C:16]([NH2:17])[C:15]2=[CH:14][N:13]=1

Participants

6

Reactant 4

HCID 2631-ButanolHCID 6422Trifluoroacetic acidHCID 8471TriethylamineHCID 68818836HCID 68818836, compound

Product 1

HCID 178509243HCID 178509243, compoundYield 59.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

N′-[5-Cyano-2-(2,4-difluoro-phenoxy)-pyrimidin-4-yl]-hydrazinecarboxylic acid tert-butyl ester (3.35 g, 9.22 mmol) was dissolved in 60 mL of dichloromethane, and 30 mL of trifluoroacetic acid was added. The reaction mixture was stirred for two and a half hours at room temperature, then concentrated under reduced pressure. 1-Butanol (90 mL) and triethylamine (6.4 mL, 46 mmol) was added to the residue, and the reaction mixture was heated to reflux with stirring for 17 hours. The reaction mixture was cooled and concentrated under reduced pressure. The residue was taken up in 300 mL and insoluble yellow solid was isolated by filtration, washing with 100 mL of dichloromethane and in vacuo, to give 1.45 g of 6-(2,4-difluoro-phenoxy)-1H-pyrazolo[3,4-d]pyrimidin-3-ylamine, MS(M+H)=264.

Workup

  1. concentrationconcentrated under reduced pressure
  2. temperaturethe reaction mixture was heated
  3. temperatureto reflux
  4. stirringwith stirring for 17 hours
  5. temperatureThe reaction mixture was cooled
  6. concentrationconcentrated under reduced pressure
  7. custominsoluble yellow solid was isolated by filtration
  8. washwashing with 100 mL of dichloromethane and in vacuo

Sources & evidence

ORD record
ord-3a0f1521448f4a86a4ca31116275618c
Source dataset
uspto-grants-2009_10
Patent number
US07601726B2

Reaction notes

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