Trifluoroacetic acid → N-(5-amino-2-methylphenyl)-4-(cyclopropylamino)thieno[3,2-d]pyrimidine-7-carboxamide

HRID 1465030Notes

Reaction equation

HRID 1465030 reaction equation
[CH:1]1([NH:4][C:5]2[C:6]3[S:13][CH:12]=[C:11]([C:14]([NH:16][C:17]4[CH:18]=[C:19]([NH:24]C(=O)OC(C)(C)C)[CH:20]=[CH:21][C:22]=4[CH3:23])=[O:15])[C:7]=3[N:8]=[CH:9][N:10]=2)[CH2:3][CH2:2]1.C(O)(C(F)(F)F)=O>C(Cl)Cl>[NH2:24][C:19]1[CH:20]=[CH:21][C:22]([CH3:23])=[C:17]([NH:16][C:14]([C:11]2[C:7]3[N:8]=[CH:9][N:10]=[C:5]([NH:4][CH:1]4[CH2:2][CH2:3]4)[C:6]=3[S:13][CH:12]=2)=[O:15])[CH:18]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 67361287t-Butyl 3-(4-(cyclopropylamino)thieno[3,2-d]pyrimidine-7-carboxamido)-4-methylphenylcarbamate

Product 1

HCID 67360673N-(5-amino-2-methylphenyl)-4-(cyclopropylamino)thieno[3,2-d]pyrimidine-7-carboxamide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

t-Butyl 3-(4-(cyclopropylamino)thieno[3,2-d]pyrimidine-7-carboxamido)-4-methylphenylcarbamate (7 g, 15.93 mmol) was dissolved in DCM (80 mL), TFA (12 mL, 159.3 mmol) was added thereto, and the mixture was stirred at room temperature for 8 hours. After the reaction was completed, the reaction mixture was concentrated under reduced pressure to remove the organic solvent and the remaining TFA, and water (20 mL) was added thereto. The reaction mixture was neutralized with 2.0 N NaOH solution, and the resulting yellow solid was filtered and dried to obtain the title compound without further purification.

Workup

  1. concentrationthe reaction mixture was concentrated under reduced pressure
  2. customto remove the organic solvent
  3. additionthe remaining TFA, and water (20 mL) was added
  4. filtrationthe resulting yellow solid was filtered
  5. customdried

Sources & evidence

ORD record
ord-e0c046fd91ce4bc289aba9f8c6b97a85
Source dataset
uspto-grants-2015_04
Patent number
US08999973B2

Reaction notes

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