Ethanol → N-(1-(4-((2-ethoxypyrimidin-4-yl)ethynyl)phenyl)propan-2-yl)acetamide

HRID 76191Notes

Reaction equation

Cl[C:2]1[N:7]=[C:6]([C:8]#[C:9][C:10]2[CH:15]=[CH:14][C:13]([CH2:16][CH:17]([NH:19][C:20](=[O:22])[CH3:21])[CH3:18])=[CH:12][CH:11]=2)[CH:5]=[CH:4][N:3]=1.[CH2:23]([OH:25])[CH3:24].[H-].[Na+]>O1CCOCC1>[CH2:23]([O:25][C:2]1[N:7]=[C:6]([C:8]#[C:9][C:10]2[CH:15]=[CH:14][C:13]([CH2:16][CH:17]([NH:19][C:20](=[O:22])[CH3:21])[CH3:18])=[CH:12][CH:11]=2)[CH:5]=[CH:4][N:3]=1)[CH3:24]

Participants

Conditions

Temperature: 0 °C

Procedure

25 mg (0.08 mmol) N-(1-(4-((2-chloropyrimidin-4-yl)ethynyl)phenyl)propan-2-yl)acetamide (170) in 1.0 mL dioxane are added to 9.3 μl (0.16 mmol) ethanol in 0.5 ml dioxane and cooled down to 0° C. 10 mg (0.24 mmol) NaH are added and the mixture is stirred at r.t. over night. The reaction is quenched with water and the solvent is evaporated in vacuo. The residue is purified by HPLC (MeOH/H2O/TFA).

Workup

customThe reaction is quenched with water
customthe solvent is evaporated in vacuo
customThe residue is purified by HPLC (MeOH/H2O/TFA)

Sources & evidence

ORD record: ord-c99b70657a8b41d5b8cecebbb3ecf696
Source dataset: uspto-grants-2014_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08835472B2

Reaction notes

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