Acetonitrile → 4-(2-(4-Nitrophenoxy)phenyl)pyrimidin-2-amine

HRID 2361077Notes

Reaction equation

CC1(C)C(C)(C)OB([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=2[O:15][C:16]2[CH:21]=[CH:20][C:19]([N+:22]([O-:24])=[O:23])=[CH:18][CH:17]=2)O1.C([O-])(=O)C.[K+].Cl[C:32]1[CH:37]=[CH:36][N:35]=[C:34]([NH2:38])[N:33]=1.C(#N)C>C(Cl)Cl.O>[N+:22]([C:19]1[CH:18]=[CH:17][C:16]([O:15][C:10]2[CH:11]=[CH:12][CH:13]=[CH:14][C:9]=2[C:32]2[CH:37]=[CH:36][N:35]=[C:34]([NH2:38])[N:33]=2)=[CH:21][CH:20]=1)([O-:24])=[O:23]

Participants

Conditions

Temperature: 85 °C

Procedure

The compound of step 1 (0.034 g, 0.054 mmol), potassium acetate (0.26 g, 2.7 mmol), 4,4,5,5-tetramethyl-2-(2-(4-nitrophenoxy)phenyl)-1,3,2-dioxaborolane (0.460 g, 1.3 mmol), and 4-chloropyrimidin-2-amine (0.17 g, 1.3 mmol) were combined in a sealed tube under nitrogen, to which 7 mL ACN and water (0.73 ml, 40 mmol) were added. The reaction was sealed and heated to 85° C. overnight. The reaction was diluted with DCM and water, and extracted 2× with DCM. The combined organics were dried over anhydrous sodium sulfate, filtered, and concentrated in vacuo. The resulting material was purified by silica gel chromatography (MeOH/DCM) to give 4-(2-(4-nitrophenoxy)phenyl)pyrimidin-2-amine as a white solid MS m/z=309 [M+H]+. Calc'd for C16H12N4O3: 308.3.

Workup

additionwere added
customThe reaction was sealed
extractionextracted 2× with DCM
dry with materialThe combined organics were dried over anhydrous sodium sulfate
filtrationfiltered
concentrationconcentrated in vacuo
customThe resulting material was purified by silica gel chromatography (MeOH/DCM)

Sources & evidence

ORD record: ord-ff2ade709f8c49d3a8cf15164a82f4ce
Source dataset: uspto-grants-2014_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08686155B2

Reaction notes

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