2-Aminopyrimidine → HCID 9973890, compound

HRID 2220062Notes

Reaction equation

[O:1]1[C:5]2[CH:6]=[CH:7][C:8]([C:10](=O)[CH:11](Br)[C:12]3[CH:17]=[CH:16][CH:15]=[C:14]([CH3:18])[N:13]=3)=[CH:9][C:4]=2[O:3][CH2:2]1.[NH2:21][C:22]1[N:27]=[CH:26][CH:25]=[CH:24][N:23]=1.C(=O)([O-])O.[Na+]>CN(C)C=O.C(OCC)(=O)C.O>[O:1]1[C:5]2[CH:6]=[CH:7][C:8]([C:10]3[N:21]=[C:22]4[N:27]=[CH:26][CH:25]=[CH:24][N:23]4[C:11]=3[C:12]3[CH:17]=[CH:16][CH:15]=[C:14]([CH3:18])[N:13]=3)=[CH:9][C:4]=2[O:3][CH2:2]1

Participants

Conditions

Temperature: 80 °C

Procedure

To a solution of 1-Benzo[1,3]dioxol-5-yl-2-bromo-2-(6-methyl-pyridin-2-yl)-ethanone of Step C (50 mg, 0.12 mmol) in dimethylformamide (1.0 mL) was added 2-aminopyrimidine (15 mg, 1.3 equiv), and sodium hydrogen carbonate (30 mg, 3 equiv). The resulting solution was shaken at 80° C. for 3 hours, diluted with ethyl acetate (2 mL) and water (3 mL). The organic extract was concentrated in vacuo and silica gel chromatography (3:1 hexane/acetone) yielded the title compound (14 mg, 35%). HPLC tR=1.75 min, LCMS 331.2 (M+1).

Workup

extractionThe organic extract
concentrationwas concentrated in vacuo and silica gel chromatography (3:1 hexane/acetone)

Sources & evidence

ORD record: ord-3f372ac82a824ceca908cc1601063c29
Source dataset: uspto-grants-2008_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07417041B2

Reaction notes

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