Water → HCID 86696695, compound

HRID 2365839Notes

Reaction equation

[CH3:1][C:2]1[N:7]=[C:6]([NH2:8])[CH:5]=[CH:4][N:3]=1.[Si:9]([O:16][CH2:17][C@@H:18]([N:27]1[CH:32]=[CH:31][C:30]([C:33]2[CH:38]=[CH:37][N:36]=[C:35](S(C)(=O)=O)[N:34]=2)=[CH:29][C:28]1=[O:43])[C:19]1[CH:24]=[CH:23][C:22]([Cl:25])=[C:21]([F:26])[CH:20]=1)([C:12]([CH3:15])([CH3:14])[CH3:13])([CH3:11])[CH3:10].O>C(O)(CC)C>[Si:9]([O:16][CH2:17][C@@H:18]([N:27]1[CH:32]=[CH:31][C:30]([C:33]2[CH:38]=[CH:37][N:36]=[C:35]([NH:8][C:6]3[CH:5]=[CH:4][N:3]=[C:2]([CH3:1])[N:7]=3)[N:34]=2)=[CH:29][C:28]1=[O:43])[C:19]1[CH:24]=[CH:23][C:22]([Cl:25])=[C:21]([F:26])[CH:20]=1)([C:12]([CH3:15])([CH3:13])[CH3:14])([CH3:11])[CH3:10]

Participants

Conditions

Temperature: 110 °C

Procedure

2-Methylpyrimidin-4-amine (0.41 g, 3.7 mmol) and (S)-1-(2-(tert-butyldimethylsilyloxy)-1-(4-chloro-3-fluorophenyl)ethyl)-4-(2-(methylsulfonyl)pyrimidin-4-yl)pyridin-2(1H)-one (0.10 g, 0.19 mmol) were placed in sec-BuOH (1 mL), heated to 110° C. in a sealed tube for 18 hours, then poured into water, and extracted with DCM. The combined organic fractions were dried (MgSO4), filtered, and concentrated to give the crude product, which was purified by column chromatography (500:5 DCM/MeOH to remove impurity, then 500:15 for product) to give (S)-1-(2-(tert-butyldimethylsilyloxy)-1-(4-chloro-3-fluorophenyl)ethyl)-4-(2-((2-methylpyrimidin-4-yl)amino)pyrimidin-4-yl)pyridin-2(1H)-one (0.034 g, 32% yield).

Workup

extractionextracted with DCM
dry with materialThe combined organic fractions were dried (MgSO4)
filtrationfiltered
concentrationconcentrated
customto give the crude product, which
customwas purified by column chromatography (500:5 DCM/MeOH
customto remove impurity

Sources & evidence

ORD record: ord-49bc915b4ae847d6bd76f47193a6222e
Source dataset: uspto-grants-2014_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08697715B2

Reaction notes

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