Trifluoroacetic acid → HCID 66742948, compound

HRID 2363947Notes

Reaction equation

HRID 2363947 reaction equation
[O:1]=[C:2]1[NH:7][C:6]2([CH2:12][CH2:11][N:10](C(OC(C)(C)C)=O)[CH2:9][CH2:8]2)[NH:5][C:4]2[CH:20]=[C:21]([C:23]3[CH:28]=[CH:27][N:26]=[CH:25][CH:24]=3)[S:22][C:3]1=2.FC(F)(F)C(O)=O.C(=O)([O-])O.[Na+].C(OCC)(=O)C>O1CCCC1>[N:26]1[CH:27]=[CH:28][C:23]([C:21]2[S:22][C:3]3[C:2](=[O:1])[NH:7][C:6]4([CH2:12][CH2:11][NH:10][CH2:9][CH2:8]4)[NH:5][C:4]=3[CH:20]=2)=[CH:24][CH:25]=1

Participants

6

Reactant 4

HCID 6422Trifluoroacetic acidHCID 8857Ethyl AcetateHCID 516892Sodium BicarbonateHCID 66743691HCID 66743691, compound

Product 1

HCID 66742948HCID 66742948, compoundYield 93%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A mixture of tert-butyl 4′-oxo-6′-(pyridin-4-yl)-3′,4′-dihydro-1′H-spiro[piperidine-4,2′-thieno[3,2-d]pyrimidine]-1-carboxylate (0.154 g, 0.385 mmol) and trifluoroacetic acid (3.0 mL) was stirred for 1 h at room temperature. The mixture was poured into sat. aqueous sodium hydrogen carbonate (100 mL), ethyl acetate (70 mL) and tetrahydrofuran (30 mL). After shaking well, the yellow precipitate was collected by filtration. This solid was suspended in ethyl acetate-dichloromethane (1:2, 10 mL) and the mixture was heated to 60° C. After 10 min, the precipitate was collected by filtration to afford the title compound (0.107 mg, 93%) as a yellow solid:

Workup

  1. stirringAfter shaking well
  2. filtrationthe yellow precipitate was collected by filtration
  3. temperaturethe mixture was heated to 60° C
  4. waitAfter 10 min
  5. filtrationthe precipitate was collected by filtration

Sources & evidence

ORD record
ord-6a4b8990bd504d6fb0f76c514bcbc702
Source dataset
uspto-grants-2014_04
Patent number
US08691828B2

Reaction notes

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