Methylamine → (S)-tert-butyl methyl(1-((5-(2-(methylamino)-4-(propylamino)pyrimidin-5-yl)-4-pentyn-1-yl)amino)-1-oxopropan-2-yl)carbamate

HRID 2284773Notes

Reaction equation

N1(O[C:11]2[N:16]=[C:15]([NH:17][CH2:18][CH2:19][CH3:20])[C:14]([C:21]#[C:22][CH2:23][CH2:24][CH2:25][NH:26][C:27](=[O:39])[C@@H:28]([N:30]([CH3:38])[C:31](=[O:37])[O:32][C:33]([CH3:36])([CH3:35])[CH3:34])[CH3:29])=[CH:13][N:12]=2)C2C=CC=CC=2N=N1.[CH3:40][NH2:41]>O1CCCC1>[CH3:38][N:30]([C@@H:28]([CH3:29])[C:27]([NH:26][CH2:25][CH2:24][CH2:23][C:22]#[C:21][C:14]1[C:15]([NH:17][CH2:18][CH2:19][CH3:20])=[N:16][C:11]([NH:41][CH3:40])=[N:12][CH:13]=1)=[O:39])[C:31](=[O:37])[O:32][C:33]([CH3:36])([CH3:34])[CH3:35]

Participants

Conditions

Temperature: 50 °C

Procedure

To (S)-tert-butyl (1-((5-(2-((1H-benzo[d][1,2,3]triazol-1-yl)oxy)-4-(propylamino)pyrimidin-5-yl)-4-pentyn-1-yl)amino)-1-oxopropan-2-yl)(methyl)carbamate (K3, 50 mg), a 2.0 mol/L solution of methylamine in tetrahydrofuran (1 mL) was added at room temperature, the reaction vessel was sealed, and then the mixture was stirred at 50° C. for 5 hours by using a microwave reaction system. The reaction mixture was cooled to room temperature, and then the solvent was evaporated under reduced pressure. The obtained residue was purified by silica gel column chromatography (eluent, 40 to 0% hexane in ethyl acetate) to obtain oily (S)-tert-butyl methyl(1-((5-(2-(methylamino)-4-(propylamino)pyrimidin-5-yl)-4-pentyn-1-yl)amino)-1-oxopropan-2-yl)carbamate (K4, 35 mg).

Workup

customthe reaction vessel was sealed
customa microwave reaction system
temperatureThe reaction mixture was cooled to room temperature
customthe solvent was evaporated under reduced pressure
customThe obtained residue was purified by silica gel column chromatography (eluent, 40 to 0% hexane in ethyl acetate)

Sources & evidence

ORD record: ord-418de67864e04681bdccc7e3b3d29233
Source dataset: uspto-grants-2015_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09145415B2

Reaction notes

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