Trifluoroacetic acid → HCID 59333770, compound

HRID 1930691Notes

Reaction equation

HRID 1930691 reaction equation
[F:1][C:2]1[CH:38]=[CH:37][CH:36]=[CH:35][C:3]=1[CH2:4][C:5]1[C:6]2[CH2:27][N:26](C(OC(C)(C)C)=O)[CH2:25][CH2:24][C:7]=2[N:8]=[C:9]([NH:11][C:12]2[CH:17]=[CH:16][C:15]([N:18]3[CH:22]=[CH:21][N:20]=[C:19]3[CH3:23])=[CH:14][CH:13]=2)[N:10]=1.C(O)(C(F)(F)F)=O.C([O-])(O)=O.[Na+]>C(Cl)Cl>[F:1][C:2]1[CH:38]=[CH:37][CH:36]=[CH:35][C:3]=1[CH2:4][C:5]1[C:6]2[CH2:27][NH:26][CH2:25][CH2:24][C:7]=2[N:8]=[C:9]([NH:11][C:12]2[CH:13]=[CH:14][C:15]([N:18]3[CH:22]=[CH:21][N:20]=[C:19]3[CH3:23])=[CH:16][CH:17]=2)[N:10]=1

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 516892Sodium BicarbonateHCID 59333742HCID 59333742, compound

Product 1

HCID 59333770HCID 59333770, compoundYield 53%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

tert-Butyl 4-(2-fluorobenzyl)-2-(4-(2-methyl-1H-imidazol-1-yl)phenylamino)-7,8-dihydropyrido[4,3-d]pyrimidine-6(5H)-carboxylate was dissolved in DCM (5 mL). TFA, 10 eq, was added and the reaction was heated to reflux for 2 h. The mixture was neutralized with sat NaHCO3 and the phases were separated. The organic phase was dried with MgSO4 and the solvent was removed under reduced pressure to yield 4-(2-fluorobenzyl)-N-(4-(2-methyl-1H-imidazol-1-yl)phenyl)-5,6,7,8-tetrahydropyrido[4,3-d]pyrimidin-2-amine (186 mg, 53%).

Workup

  1. temperaturethe reaction was heated
  2. temperatureto reflux for 2 h
  3. customthe phases were separated
  4. dry with materialThe organic phase was dried with MgSO4
  5. customthe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-eea366bbdf7f429dbeb03a2ac602039e
Source dataset
uspto-grants-2012_05
Patent number
US08188101B2

Reaction notes

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