3-(Cyclopropylamino)propionitrile → tert-Butyl 4-((2-cyanoethyl)(cyclopropyl)amino)-2-(4-(2-methyl-1H-imidazol-1-yl)phenylamino)-7,8-dihydropyrido[4,3-d]pyrimidine-6(5H)-carboxylate

HRID 1930659Notes

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

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). 3-(cyclopropylamino)propanenitrile (49.7 mg, 0.45 mmol) was added and the reaction mixture was stirred at 85° C. overnight. The mixture was allowed to reach room temperature and the solvent was evaporated under reduced pressure. The crude tert-butyl 4-((2-cyanoethyl)(cyclopropyl)amino)-2-(4-(2-methyl-1H-imidazol-1-yl)phenylamino)-7,8-dihydropyrido[4,3-d]pyrimidine-6 (5H)-carboxylate (241 mg, 104%) was used as such in the subsequent step.

Workup

customto reach room temperature
customthe solvent was evaporated under reduced pressure

Sources & evidence

ORD record: ord-f77c07787dec4802b9b4bc188bd9d023
Source dataset: uspto-grants-2012_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08188101B2

Reaction notes

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