Trifluoroacetic acid → [4-fluoro-2-(tetrahydro-2H-pyran-4-yloxy)-phenyl]-(5,6,7,8-tetrahydro-pyrido[4',3':4,5]thieno[2,3-d]pyrimidin-4-yl)-amine

HRID 450574Notes

Reaction equation

HRID 450574 reaction equation
FC(F)(F)C(O)=O.C(OC([N:15]1[CH2:42][CH2:41][C:18]2[C:19]3[C:24]([NH:25][C:26]4[CH:31]=[CH:30][C:29]([F:32])=[CH:28][C:27]=4[O:33][CH:34]4[CH2:39][CH2:38][O:37][CH2:36][CH2:35]4)=[N:23][CH:22]=[N:21][C:20]=3[S:40][C:17]=2[CH2:16]1)=O)(C)(C)C>C(Cl)Cl>[F:32][C:29]1[CH:30]=[CH:31][C:26]([NH:25][C:24]2[C:19]3[C:18]4[CH2:41][CH2:42][NH:15][CH2:16][C:17]=4[S:40][C:20]=3[N:21]=[CH:22][N:23]=2)=[C:27]([O:33][CH:34]2[CH2:39][CH2:38][O:37][CH2:36][CH2:35]2)[CH:28]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 696691144-[4-Fluoro-2-(tetrahydro-2H-pyran-4-yloxy)-phenylamino]-5,8-dihydro-6H-pyrido[4',3':4,5]thieno[2,3-d]pyrimidine-7-carboxylic acid tert-butyl ester

Product 1

HCID 46182217[4-fluoro-2-(tetrahydro-2H-pyran-4-yloxy)-phenyl]-(5,6,7,8-tetrahydro-pyrido[4',3':4,5]thieno[2,3-d]pyrimidin-4-yl)-amineYield 66.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

Trifluoroacetic acid (0.50 mL) was added into a solution of 4-[4-fluoro-2-(tetrahydro-2H-pyran-4-yloxy)-phenylamino]-5,8-dihydro-6H-pyrido[4′,3′:4,5]thieno[2,3-d]pyrimidine-7-carboxylic acid tert-butyl ester (0.031 g, 0.06 mmol) in DCM (1 mL) and the reaction mixture was stirred at ambient temperature for 2 hours. The reaction mixture was diluted with DCM and washed with 2M NaOH. The organic phase was dried (MgSO4), filtered and concentrated in vacuo. The residue was washed with hexane to afford the title compound as a white solid (0.016 g, 65%).

Workup

  1. washwashed with 2M NaOH
  2. dry with materialThe organic phase was dried (MgSO4)
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo
  5. washThe residue was washed with hexane

Sources & evidence

ORD record
ord-df3ac11150174c7dbffd833b59a82f48
Source dataset
uspto-grants-2013_07
Patent number
US08486953B2

Reaction notes

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