N-Ethyltetrahydrofurfurylamine → tert-Butyl 4-(ethyl((tetrahydrofuran-2-yl)methyl)amino)-2-(4-(2-methyl-1H-imidazol-1-yl)phenylamino)-7,8-dihydropyrido[4,3-d]pyrimidine-6(5H)-carboxylate

HRID 1930656Notes

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.[O:39]1[CH2:43][CH2:42][CH2:41][CH:40]1[CH2:44][NH:45][CH2:46][CH3:47]>CN(C=O)C>[CH2:46]([N:45]([CH2:44][CH:40]1[CH2:41][CH2:42][CH2:43][O:39]1)[C:16]1[C:17]2[CH2:23][N:22]([C:24]([O:26][C:27]([CH3:30])([CH3:28])[CH3:29])=[O:25])[CH2:21][CH2:20][C:18]=2[N:19]=[C:14]([NH:13][C:10]2[CH:9]=[CH:8][C:7]([N:3]3[CH:4]=[CH:5][N:6]=[C:2]3[CH3:1])=[CH:12][CH:11]=2)[N:15]=1)[CH3:47]

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, example 69c) was dissolved in DMF (2 mL). N-((tetrahydrofuran-2-yl)methyl)ethanamine (58.2 mg, 0.45 mmol) was added and the reaction mixture was stirred at 85° C. overnight. The reaction was allowed to reach room temperature, the solvent was evaporated under reduced pressure and the crude was used as such in the subsequent step. MS (ES+) m/z 534.4 (M+H)+

Workup

customto reach room temperature
customthe solvent was evaporated under reduced pressure

Sources & evidence

ORD record: ord-25c008e5f159425fb54c3094a57ea57d
Source dataset: uspto-grants-2012_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08188101B2

Reaction notes

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