Hydrochloric Acid → 1-(2-(3-Methoxy-4-(4-methyl-1H-imidazol-1-yl)phenylamino)-6-((2,2,2-trifluoroethoxy)-methyl)pyrimidin-4-yl)ethanone

HRID 59076Notes

Reaction equation

C([O:3][C:4]([C:6]1[CH:11]=[C:10]([CH2:12][O:13][CH2:14][C:15]([F:18])([F:17])[F:16])[N:9]=[C:8]([NH:19][C:20]2[CH:25]=[CH:24][C:23]([N:26]3[CH:30]=[C:29]([CH3:31])[N:28]=[CH:27]3)=[C:22]([O:32][CH3:33])[CH:21]=2)[N:7]=1)=[CH2:5])C.Cl.C(=O)(O)[O-].[Na+]>>[CH3:33][O:32][C:22]1[CH:21]=[C:20]([NH:19][C:8]2[N:7]=[C:6]([C:4](=[O:3])[CH3:5])[CH:11]=[C:10]([CH2:12][O:13][CH2:14][C:15]([F:16])([F:17])[F:18])[N:9]=2)[CH:25]=[CH:24][C:23]=1[N:26]1[CH:30]=[C:29]([CH3:31])[N:28]=[CH:27]1

Participants

Reactant 3

HCID 313Hydrochloric Acid

HCID 516892Sodium Bicarbonate

HCID 1178242434-(1-Ethoxyvinyl)-N-(3-methoxy-4-(4-methyl-1H-imidazol-1-yl)phenyl)-6-((2,2,2-trifluoroethoxy)methyl)pyrimidin-2-amine

Product 1

HCID 1178240761-(2-(3-Methoxy-4-(4-methyl-1H-imidazol-1-yl)phenylamino)-6-((2,2,2-trifluoroethoxy)-methyl)pyrimidin-4-yl)ethanoneYield 99.5%

Conditions

Temperature: 60 °C

Procedure

To a solution of 4-(1-ethoxyvinyl)-N-(3-methoxy-4-(4-methyl-1H-imidazol-1-yl)phenyl)-6-((2,2,2-trifluoroethoxy)methyl)pyrimidin-2-amine (0.418 g, 0.90 mmol) dioxane (60 mL) water 3 mL) and concentrated hydrochloric acid (0.228 mL, 2.71 mmol) were added. The solution was heated at 60° C. for 15 min. The mixture was treated with an excess of sodium bicarbonate and extracted twice with ethyl acetate. The combined organic phase was dried over sodium sulfate and concentrated to yield the title product as a solid 390 mg (99%).

Workup

extractionextracted twice with ethyl acetate
dry with materialThe combined organic phase was dried over sodium sulfate
concentrationconcentrated

Sources & evidence

ORD record: ord-1fd55228e0ae4357bbdeb29b83f19aa0
Source dataset: uspto-grants-2016_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09439904B2

Reaction notes

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