Exo-2-bornanamine → n4-((2r)-Bicyclo[2.2.1]heptan-2-yl)-6-methyl-n2-(4-(2-methyl-1h-imidazol-1-yl)phenyl)-5,6,7,8-tetrahydropyrido[4,3-d]pyrimidine-2,4-diamine

HRID 1930554Notes

Reaction equation

[CH2:1]1[CH:5]2[CH2:6][CH:7]([NH2:8])[CH:3]([CH2:4]2)[CH2:2]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>C(Cl)Cl>[CH:3]12[CH2:4][CH:5]([CH2:1][CH2:2]1)[CH2:6][C@H:7]2[NH:8][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:23]=[CH:24][C:25]([N:28]3[CH:32]=[CH:31][N:30]=[C:29]3[CH3:33])=[CH:26][CH:27]=2)[N:20]=1

Participants

Conditions

Temperature: 35 °C

Procedure

exo-2-Aminonorbornane (20.24 μl, 0.17 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 (80 mg, 0.17 mmol, Example 9a) in DCM (10 mL). The reaction was stirred at 35° C. for 2 h. Solvent was evaporated and the crude mixture dissolved in MeOH/DMSO and purified on preparative HPLC to give N4-((2R)-bicyclo[2.2.1]heptan-2-yl)-6-methyl-N2-(4-(2-methyl-1H-imidazol-1-yl)phenyl)-5,6,7,8-tetrahydropyrido[4,3-d]pyrimidine-2,4-diamine (40.0 mg, 47.8%).

Workup

customSolvent was evaporated
dissolutionthe crude mixture dissolved in MeOH/DMSO
custompurified on preparative HPLC

Sources & evidence

ORD record: ord-34c66d04dbd94046a9053293d271ddba
Source dataset: uspto-grants-2012_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08188101B2

Reaction notes

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