Trifluoroacetic acid → 4-(1-(3,5-dimethyl-1H-pyrazol-1-yl)ethyl)-N-(3-methoxy-4-(4-methyl-1H-imidazol-1-yl)phenyl)-5,6,7,8-tetrahydropyrido[4,3-d]pyrimidin-2-amine

HRID 1930713Notes

Reaction equation

HRID 1930713 reaction equation
[CH3:1][C:2]1[CH:6]=[C:5]([CH3:7])[N:4]([CH:8]([C:10]2[C:11]3[CH2:34][N:33](C(OC(C)(C)C)=O)[CH2:32][CH2:31][C:12]=3[N:13]=[C:14]([NH:16][C:17]3[CH:22]=[CH:21][C:20]([N:23]4[CH:27]=[C:26]([CH3:28])[N:25]=[CH:24]4)=[C:19]([O:29][CH3:30])[CH:18]=3)[N:15]=2)[CH3:9])[N:3]=1.C(O)(C(F)(F)F)=O.C([O-])(O)=O.[Na+]>C(Cl)Cl>[CH3:1][C:2]1[CH:6]=[C:5]([CH3:7])[N:4]([CH:8]([C:10]2[C:11]3[CH2:34][NH:33][CH2:32][CH2:31][C:12]=3[N:13]=[C:14]([NH:16][C:17]3[CH:22]=[CH:21][C:20]([N:23]4[CH:27]=[C:26]([CH3:28])[N:25]=[CH:24]4)=[C:19]([O:29][CH3:30])[CH:18]=3)[N:15]=2)[CH3:9])[N:3]=1

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 516892Sodium BicarbonateHCID 59333720HCID 59333720, compound

Product 1

HCID 593337574-(1-(3,5-dimethyl-1H-pyrazol-1-yl)ethyl)-N-(3-methoxy-4-(4-methyl-1H-imidazol-1-yl)phenyl)-5,6,7,8-tetrahydropyrido[4,3-d]pyrimidin-2-amineYield 77%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of tert-butyl 4-(1-(3,5-dimethyl-1H-pyrazol-1-yl)ethyl)-2-(3-methoxy-4-(4-methyl-1H-imidazol-1-yl)phenylamino)-7,8-dihydropyrido[4,3-d]pyrimidine-6(5H)-carboxylate (397 mg, 0.71 mmol) and TFA (0.547 mL, 7.10 mmol) in DCM was stirred for one hour at 40° C. The reaction mixture was cooled and sat aqu NaHCO3 was added until the mixture was neutralized. The organic phase was separated and the water phase was washed repeatedly with DCM yielding 4-(1-(3,5-dimethyl-1H-pyrazol-1-yl)ethyl)-N-(3-methoxy-4-(4-methyl-1H-imidazol-1-yl)phenyl)-5,6,7,8-tetrahydropyrido[4,3-d]pyrimidin-2-amine (250 mg, 77%)

Workup

  1. temperatureThe reaction mixture was cooled
  2. additionwas added until the mixture
  3. customThe organic phase was separated
  4. washthe water phase was washed repeatedly with DCM

Sources & evidence

ORD record
ord-0d45801f58374ca899b67bdb19bf4e6f
Source dataset
uspto-grants-2012_05
Patent number
US08188101B2

Reaction notes

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