Trifluoroacetic acid → HCID 57708328, compound

HRID 1014123Notes

Reaction equation

HRID 1014123 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[CH2:26][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[CH2:26][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 66769367HCID 66769367, compound

Product 1

HCID 57708328HCID 57708328, compoundYield 36%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of tert-butyl 3-(6-(4-phenoxyphenylamino)pyrimidin-4-ylamino)pyrrolidin-1-carboxylate (0.1 g, 0.2 mmol) in dry CH2Cl2 (2.0 mL) at 0° C. was added CF3COOH (2 mL, 20 vol.) and the reaction mixture was kept at this temperature for 30 min. It was allowed to come to rt and stir at this temperature for 3 h. The reaction mixture was concentrated under reduced pressure and the residue was quenched with water (2 mL), basified with NaHCO3 solution, and was extracted with ethyl acetate (2×8 mL). The combined ethyl acetate extract was washed with water (2 mL) and brine (2 mL), was dried over Na2SO4 and was concentrated under reduced pressure to give N4-(4-phenoxyphenyl)-N6-(pyrrolidin-3-yl)pyrimidine-4,6-diamine (0.025 g, 32.4%) as a light a brown 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) and brine (2 mL)
  7. dry with materialwas dried over Na2SO4
  8. concentrationwas concentrated under reduced pressure

Sources & evidence

ORD record
ord-c30fee1421a3424fad60cf93cccb842a
Source dataset
uspto-grants-2011_07
Patent number
US07982036B2

Reaction notes

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