Trifluoroacetic acid → HCID 57708327, compound

HRID 2093513Notes

Reaction equation

HRID 2093513 reaction equation
[O:1]([C:8]1[CH:13]=[CH:12][C:11]([NH:14][C:15]2[N:20]=[CH:19][N:18]=[C:17]([NH:21][CH:22]3[CH2:27][CH2:26][CH2:25][N:24](C(OC(C)(C)C)=O)[CH2:23]3)[CH:16]=2)=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(O)(C(F)(F)F)=O>C(Cl)Cl>[O:1]([C:8]1[CH:9]=[CH:10][C:11]([NH:14][C:15]2[CH:16]=[C:17]([NH:21][CH:22]3[CH2:27][CH2:26][CH2:25][NH:24][CH2:23]3)[N:18]=[CH:19][N:20]=2)=[CH:12][CH:13]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 57708276HCID 57708276, compound

Product 1

HCID 57708327HCID 57708327, compoundYield 81.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of tert-butyl 3-(6-(4-phenoxyphenylamino)pyrimidin-4-ylamino)piperidine-1-carboxylate (110 mg, 0.238 mmol) in dry CH2Cl2 (1.0 mL) at 0° C. was added CF3COOH (0.5 mL, 5 vol) and the reaction mixture was kept at this temperature for 30 min. It was allowed to come to rt and to stir at this temperature for 3 h. The reaction mixture was concentrated under reduced pressure and the residue was quenched with water (2 mL), was basified with NaHCO3 solution, and was extracted with ethyl acetate (2×8 mL). The combined ethyl acetate extract was washed with water (2 mL), brine (2 mL), dried over Na2SO4 and concentrated under reduced pressure to give N4-(4-phenoxyphenyl)-N6-(piperidin-3-yl)pyrimidine-4,6-diamine (0.07 g, 81%) as a light yellow solid.

Workup

  1. customto come to rt
  2. concentrationThe reaction mixture was concentrated under reduced pressure
  3. customthe residue was quenched with water (2 mL)
  4. extractionwas extracted with ethyl acetate (2×8 mL)
  5. extractionThe combined ethyl acetate extract
  6. washwas washed with water (2 mL), brine (2 mL)
  7. dry with materialdried over Na2SO4
  8. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-cf0694b4f2784ab6acda537be4d050cf
Source dataset
uspto-grants-2013_05
Patent number
US08445498B2

Reaction notes

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