Lithium Hydroxide → HCID 66609034, compound

HRID 1772156Notes

Reaction equation

[C:1]([C:5]1[S:6][C:7]([CH2:14][NH:15][C:16]2[CH:21]=[CH:20][CH:19]=[C:18]([C:22]3[CH:27]=[C:26]([NH:28][C:29]4[CH:34]=[CH:33][N:32]=[CH:31][N:30]=4)[C:25](=[O:35])[N:24]([CH3:36])[CH:23]=3)[C:17]=2[CH2:37][O:38][Si:39]([C:42]([CH3:45])([CH3:44])[CH3:43])([CH3:41])[CH3:40])=[C:8]([C:10]([O:12]C)=[O:11])[N:9]=1)([CH3:4])([CH3:3])[CH3:2].[OH-].[Li+]>C(O)(C)C.O>[C:1]([C:5]1[S:6][C:7]([CH2:14][NH:15][C:16]2[CH:21]=[CH:20][CH:19]=[C:18]([C:22]3[CH:27]=[C:26]([NH:28][C:29]4[CH:34]=[CH:33][N:32]=[CH:31][N:30]=4)[C:25](=[O:35])[N:24]([CH3:36])[CH:23]=3)[C:17]=2[CH2:37][O:38][Si:39]([C:42]([CH3:45])([CH3:44])[CH3:43])([CH3:41])[CH3:40])=[C:8]([C:10]([OH:12])=[O:11])[N:9]=1)([CH3:4])([CH3:2])[CH3:3]

Participants

Conditions

Temperature: 25 °C

Procedure

A mixture of methyl 2-tert-butyl-5-((2-((tert-butyldimethylsilyloxy)methyl)-3-(1-methyl-6-oxo-5-(pyrimidin-4-ylamino)-1,6-dihydropyridin-3-yl)phenylamino)-methyl)thiazole-4-carboxylate (125d) (590 mg, 0.9 mmol) and lithium hydroxide (1090 mg, 45 mmol) in isopropyl alcohol (20 mL) and water (20 mL) was stirred at 25° C. for 5 h. The reaction mixture was concentrated to about 50% of the original volume and acidified to pH˜4 with 1M HCl (aq.). It was then extracted with CH2Cl2:MeOH(−7:1). The organic layers were combined, dried with anhydrous MgSO4, and concentrated to afford 125e, which was used in the next step without further purification. LCMS: (M+H)+ 635.

Workup

concentrationThe reaction mixture was concentrated to about 50% of the original volume
extractionIt was then extracted with CH2Cl2
dry with materialdried with anhydrous MgSO4
concentrationconcentrated

Sources & evidence

ORD record: ord-1b42b0c9520f425dac0ebe7f0ba33b15
Source dataset: uspto-grants-2016_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09249123B2

Reaction notes

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