Diisopropylethylamine → 4-(((1R,4S)-4-hydroxy-3,3-dimethylcyclohexyl)amino)-2-((2-(5-methoxypyridin-3-yl)ethyl)amino)pyrimidine-5-carbonitrile

HRID 1749554Notes

Reaction equation

[OH:1][C@H:2]1[CH2:7][CH2:6][C@@H:5]([NH:8][C:9]2[C:14]([C:15]#[N:16])=[CH:13][N:12]=[C:11](S(C)=O)[N:10]=2)[CH2:4][C:3]1([CH3:21])[CH3:20].Cl.Cl.[CH3:24][O:25][C:26]1[CH:27]=[C:28]([CH2:32][CH2:33][NH2:34])[CH:29]=[N:30][CH:31]=1.CCN(C(C)C)C(C)C>CS(C)=O>[OH:1][C@H:2]1[CH2:7][CH2:6][C@@H:5]([NH:8][C:9]2[C:14]([C:15]#[N:16])=[CH:13][N:12]=[C:11]([NH:34][CH2:33][CH2:32][C:28]3[CH:29]=[N:30][CH:31]=[C:26]([O:25][CH3:24])[CH:27]=3)[N:10]=2)[CH2:4][C:3]1([CH3:21])[CH3:20]

Participants

Conditions

Temperature: 60 °C

Procedure

A 1 dram vial equipped with a septum cap was charged with 4-(((1R,4S)-4-hydroxy-3,3-dimethylcyclohexyl)amino)-2-(methylsulfinyl)pyrimidine-5-carbonitrile (55.0 mg, 0.178 mmol), 2-(5-methoxypyridin-3-yl)ethan-1-amine dihydrochloride (56.3 mg, 0.214 mmol) and DMSO (1.4 mL). The resulting solution was treated with DIEA (0.125 mL, 0.715 mmol), and the vial was sealed and shaken (250 rpm) at 60° C. for 14 h. The mixture was cooled to room temperature, diluted with DMSO (1.5 mL), and filtered. The solution was purified by standard methods to provide the title compound. MS (ESI) m/z 379.2 [M+1]1.

Workup

customA 1 dram vial equipped with a septum
customcap
customthe vial was sealed
temperatureThe mixture was cooled to room temperature
filtrationfiltered
customThe solution was purified by standard methods

Sources & evidence

ORD record: ord-8c6bb7d46ad7450c951b8465d04b0b91
Source dataset: uspto-grants-2015_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09156798B2

Reaction notes

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