Trifluoroacetic acid → 4-Phenyl-5,6,7,8-tetrahydropyrido[3,4-d]pyrimidine

HRID 510220Notes

Reaction equation

HRID 510220 reaction equation
[C:1]1([C:7]2[C:8]3[CH2:16][CH2:15][NH:14][CH2:13][C:9]=3[N:10]=[CH:11][N:12]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C(O)(C(F)(F)F)=O>C(Cl)Cl>[NH3:10].[C:1]1([C:7]2[C:8]3[CH2:16][CH2:15][NH:14][CH2:13][C:9]=3[N:10]=[CH:11][N:12]=2)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

5

Reactant 2

HCID 6422Trifluoroacetic acidHCID 583781534-Phenyl-5,6,7,8-tetrahydropyrido[3,4-d]pyrimidine

Product 2

HCID 222AmmoniaHCID 583781534-Phenyl-5,6,7,8-tetrahydropyrido[3,4-d]pyrimidineYield 96%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To the product of Intermediate 1, step c (265 mg, 0.85 mmol) in DCM (4 mL) was added TFA (0.85 mL). After stirring 3 h, the mixture was concentrated in vacuo. The residue was dissolved in DCM and treated with saturated aqueous NaHCO3 solution. The aqueous layer was then extracted with DCM and EtOAc. The combined organic layers were dried over Na2SO4, filtered and concentrated in vacuo. Chromatography on SiO2 eluting with 2 M NH3 in MeOH/DCM afforded the desired product as a dark orange oil (172 mg, 96%). MS (ESI) mass calcd. C13H13N3, 211.11. m/z found 212.1 [M+H]+. 1H NMR (500 MHz, CDCl3): 9.03 (s, 1H), 7.62-7.56 (m, 2H), 7.52-7.43 (m, 3H), 4.16 (s, 2H), 3.09 (t, J=5.7 Hz, 2H), 2.85 (t, J=5.6 Hz, 2H).

Workup

  1. concentrationthe mixture was concentrated in vacuo
  2. dissolutionThe residue was dissolved in DCM
  3. additiontreated with saturated aqueous NaHCO3 solution
  4. extractionThe aqueous layer was then extracted with DCM and EtOAc
  5. dry with materialThe combined organic layers were dried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-daa929b085e14c8e8aab72f4215ff0f5
Source dataset
uspto-grants-2015_08
Patent number
US09096596B2

Reaction notes

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