Cyclohexylamine → tert-Butyl 4-(cyclohexylamino)-2-(4-(2-methyl-1H-imidazol-1-yl)phenylamino)-7,8-dihydropyrido[4,3-d]pyrimidine-6(5H)-carboxylate

HRID 1930636Notes

Reaction equation

[CH3:1][C:2]1[N:3]([C:7]2[CH:12]=[CH:11][C:10]([NH:13][C:14]3[N:15]=[C:16](OS(C(F)(F)F)(=O)=O)[C:17]4[CH2:23][N:22]([C:24]([O:26][C:27]([CH3:30])([CH3:29])[CH3:28])=[O:25])[CH2:21][CH2:20][C:18]=4[N:19]=3)=[CH:9][CH:8]=2)[CH:4]=[CH:5][N:6]=1.[CH:39]1([NH2:45])[CH2:44][CH2:43][CH2:42][CH2:41][CH2:40]1>CN(C=O)C>[CH:39]1([NH:45][C:16]2[C:17]3[CH2:23][N:22]([C:24]([O:26][C:27]([CH3:30])([CH3:28])[CH3:29])=[O:25])[CH2:21][CH2:20][C:18]=3[N:19]=[C:14]([NH:13][C:10]3[CH:9]=[CH:8][C:7]([N:3]4[CH:4]=[CH:5][N:6]=[C:2]4[CH3:1])=[CH:12][CH:11]=3)[N:15]=2)[CH2:44][CH2:43][CH2:42][CH2:41][CH2:40]1

Participants

Conditions

Temperature: 85 °C

Procedure

tert-Butyl 2-(4-(2-methyl-1H-imidazol-1-yl)phenylamino)-4-(trifluoromethylsulfonyloxy)-7,8-dihydropyrido[4,3-d]pyrimidine-6(5H)-carboxylate (250 mg, 0.45 mmol) was dissolved in DMF (2 mL). Cyclohexanamine (44.7 mg, 0.45 mmol) was added and the reaction mixture was heated at 85° C. overnight. The reaction mixture was allowed to reach room temperature, the solvent was evaporated under reduced pressure and the crude was purified by flash chromatography using dichloromethane and methanol as eluent yielding tert-butyl 4-(cyclohexylamino)-2-(4-(2-methyl-1H-imidazol-1-yl)phenylamino)-7,8-dihydropyrido[4,3-d]pyrimidine-6(5H)-carboxylate (124 mg, 54.6%). MS (ES+) m/z 504.4 (M+H)+

Workup

customto reach room temperature
customthe solvent was evaporated under reduced pressure
customthe crude was purified by flash chromatography

Sources & evidence

ORD record: ord-33455f426b1e4c71b503ce3eb8972599
Source dataset: uspto-grants-2012_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08188101B2

Reaction notes

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