Trifluoroacetic acid → HCID 57848884, compound

HRID 2188993Notes

Reaction equation

HRID 2188993 reaction equation
[Cl:1][C:2]1[N:3]=[C:4](Cl)[C:5]2[S:10][CH:9]=[CH:8][C:6]=2[N:7]=1.C(O)(C(F)(F)F)=O.[CH3:19][C:20]1[CH:26]=[C:25]([CH3:27])[CH:24]=[C:23]([CH3:28])[C:21]=1[NH2:22]>C(Cl)Cl>[Cl:1][C:2]1[N:3]=[C:4]([NH:22][C:21]2[C:23]([CH3:28])=[CH:24][C:25]([CH3:27])=[CH:26][C:20]=2[CH3:19])[C:5]2[S:10][CH:9]=[CH:8][C:6]=2[N:7]=1

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 69132,4,6-TrimethylanilineHCID 127128322,4-Dichlorothieno[3,2-d]pyrimidine

Product 1

HCID 57848884HCID 57848884, compoundYield 23.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
90 °C

Procedure

To a solution of 2,4-dichlorothieno[3,2-d]pyrimidine (148 mg, 0.73 mmol), TFA (0.17 mL, 2.19 mmol) in TFE (2 mL) was added 2,4,6-trimethylaniline (0.15 mg, 1.1 mmol) in a sealed tube. The reaction was stirred at 90° C. for 15 h. The reaction mixture was diluted with CH2Cl2 and washed with saturated NaHCO3 solution (3×20 mL). The combined organic layers were washed with brine, dried over Na2SO4, filtered, and concentrated in vacuo. The crude product was purified by column chromatography eluting with Hexanes:ethyl acetate (4:1) to afford the product as a white solid (51.4 mg, 23%):

Workup

  1. washwashed with saturated NaHCO3 solution (3×20 mL)
  2. washThe combined organic layers were washed with brine
  3. dry with materialdried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customThe crude product was purified by column chromatography
  7. washeluting with Hexanes:ethyl acetate (4:1)

Sources & evidence

ORD record
ord-530e9dfe2797480fab2136bdfb357ba6
Source dataset
uspto-grants-2012_12
Patent number
US08324223B2

Reaction notes

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