N-Methylcyclohexylamine → N4-cyclohexyl-N4,6-dimethyl-N2-(4-(2-methyl-1H-imidazol-1-yl)phenyl)-5,6,7,8-tetrahydropyrido[4,3-d]pyrimidine-2,4-diamine

HRID 1930555Notes

Reaction equation

HRID 1930555 reaction equation
[CH3:1][NH:2][CH:3]1[CH2:8][CH2:7][CH2:6][CH2:5][CH2:4]1.FC(F)(F)S(O[C:15]1[C:16]2[CH2:37][N:36]([CH3:38])[CH2:35][CH2:34][C:17]=2[N:18]=[C:19]([NH:21][C:22]2[CH:27]=[CH:26][C:25]([N:28]3[CH:32]=[CH:31][N:30]=[C:29]3[CH3:33])=[CH:24][CH:23]=2)[N:20]=1)(=O)=O>CS(C)=O>[CH:3]1([N:2]([CH3:1])[C:15]2[C:16]3[CH2:37][N:36]([CH3:38])[CH2:35][CH2:34][C:17]=3[N:18]=[C:19]([NH:21][C:22]3[CH:27]=[CH:26][C:25]([N:28]4[CH:32]=[CH:31][N:30]=[C:29]4[CH3:33])=[CH:24][CH:23]=3)[N:20]=2)[CH2:8][CH2:7][CH2:6][CH2:5][CH2:4]1

Participants

4

Reactant 2

HCID 7514N-MethylcyclohexylamineHCID 593337246-methyl-2-(4-(2-methyl-1H-imidazol-1-yl)phenylamino)-5,6,7,8-tetrahydropyrido[4,3-d]pyrimidin-4-yl trifluoromethanesulfonate

Product 1

HCID 46200351N4-cyclohexyl-N4,6-dimethyl-N2-(4-(2-methyl-1H-imidazol-1-yl)phenyl)-5,6,7,8-tetrahydropyrido[4,3-d]pyrimidine-2,4-diamineYield 59.7%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
80 °C

Procedure

N-Methylcyclohexanamine (9.67 mg, 0.09 mmol) was added to a solution of 6-methyl-2-(4-(2-methyl-1H-imidazol-1-yl)phenylamino)-5,6,7,8-tetrahydropyrido[4,3-d]pyrimidin-4-yl trifluoromethanesulfonate (40 mg, 0.09 mmol, Example 9a) in DMSO (1 mL) and the reaction was stirred at 80° C. for 2 h. Solvent was allowed to cool down, filtered and the product purified on preparative HPLC to give N4-cyclohexyl-N4,6-dimethyl-N2-(4-(2-methyl-1H-imidazol-1-yl)phenyl)-5,6,7,8-tetrahydropyrido[4,3-d]pyrimidine-2,4-diamine (22.00 mg, 59.7%). MS (ESI+)/(ESI−) m/z 432/430

Workup

  1. temperatureto cool down
  2. filtrationfiltered
  3. customthe product purified on preparative HPLC

Sources & evidence

ORD record
ord-3d2f724d3d5e4b5aa4f30f380e7af67a
Source dataset
uspto-grants-2012_05
Patent number
US08188101B2

Reaction notes

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