Diisopropylethylamine → 1009036-31-0

HRID 2244054Notes

Reaction equation

HRID 2244054 reaction equation
F[C:2]1[C:9]([F:10])=[C:8]([F:11])[CH:7]=[CH:6][C:3]=1[C:4]#[N:5].C(O)(=O)C.[CH:16](N)=[NH:17].C([N:22](C(C)C)CC)(C)C>CC(N(C)C)=O>[F:11][C:8]1[C:9]([F:10])=[C:2]2[C:3]([C:4]([NH2:22])=[N:5][CH:16]=[N:17]2)=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 160693Formamidine acetateHCID 5189362,3,4-Trifluorobenzonitrile

Product 1

HCID 250594341009036-31-0Yield 43.4%

Reagents, catalysts & solvents 1

HCID 31374DimethylacetamideSolvent

Procedure

2,3,4-Trifluoro-benzonitrile (3.00 g, 19.1 mmol) is mixed with dimethylacetamide (30 mL). Formamidine acetate (1.99 g, 19.1 mmol) and diisopropylethyl amine (10 mL, 57.3 mmol) are added, and the resulting reaction mixture is slowly heated. Upon heating, the starting heterogeneous mixture slowly turns into a homogeneous solution. At 80° C., precipitates start to form. The reaction mixture proceeds at 80° C. for ˜30 minutes before it is cooled and filtered. The collected solid is further washed with DCM to afford 1.50 g of 7,8-Difluoro-quinazolin-4-ylamine (43% yield) as white solid. LC/MS found m/z=182 [M+H]+.

Workup

  1. customthe resulting reaction mixture
  2. temperatureis slowly heated
  3. temperatureUpon heating
  4. customAt 80° C., precipitates
  5. customto form
  6. temperatureis cooled
  7. filtrationfiltered
  8. washThe collected solid is further washed with DCM

Sources & evidence

ORD record
ord-dfed10b3dd7e4070bd2ae0a838d62807
Source dataset
uspto-grants-2010_03
Patent number
US07678803B2

Reaction notes

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