Trifluoroacetic acid → 2-Chloro-N-mesitylthieno[2,3-d]pyrimidin-4-amine

HRID 1509959Notes

Reaction equation

HRID 1509959 reaction equation
[Cl:1][C:2]1[N:3]=[C:4](Cl)[C:5]2[CH:10]=[CH:9][S: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[CH:10]=[CH:9][S:8][C:6]=2[N:7]=1

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 69132,4,6-TrimethylanilineHCID 122173242,4-Dichlorothieno[2,3-d]pyrimidine

Product 1

HCID 578488852-Chloro-N-mesitylthieno[2,3-d]pyrimidin-4-amineYield 36%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
90 °C

Procedure

To a solution of 2,4-dichlorothieno[2,3-d]pyrimidine (805 mg, 3.94 mmol), TFA (0.91 mL, 11.82 mmol) in TFE (11 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 2 d. Reaction mixture was diluted with CH2Cl2 and washed with saturated NaHCO3 (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 HPLC to afford the product as a white solid (43.4 mg, 36%):

Workup

  1. customReaction mixture
  2. washwashed with saturated NaHCO3 (3×20 mL)
  3. washThe combined organic layers were washed with brine
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customThe crude product was purified by HPLC

Sources & evidence

ORD record
ord-1a62d2640196485bb3528cbe5c5e2483
Source dataset
uspto-grants-2012_07
Patent number
US08211898B2

Reaction notes

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