4-Amino-6-chloropyrimidine → HCID 86710137, compound

HRID 1468304Notes

Reaction equation

[NH2:1][C:2]1[CH:7]=[C:6]([Cl:8])[N:5]=[CH:4][N:3]=1.Br[CH2:10][C:11](=O)[CH:12]([CH3:14])[CH3:13].C(=O)([O-])O.[Na+]>CN(C=O)C>[Cl:8][C:6]1[N:5]=[CH:4][N:3]2[CH:10]=[C:11]([CH:12]([CH3:14])[CH3:13])[N:1]=[C:2]2[CH:7]=1

Participants

Conditions

Temperature: 50 °C

Procedure

4-Amino-6-chloropyrimidine (100 mg, 0.772 mmol) was suspended in DMF (0.5 mL), and the suspension was stirred overnight at 50° C. after adding 1-bromo-3-methylbutan-2-one (153 mg, 0.920 mmol) and molecular sieve 4A (200 mg). The reaction mixture was allowed to cool to room temperature. After adding a sodium hydrogen carbonate aqueous solution, the mixture was filtered through Celite (registered trademark), and extracted with ethyl acetate. The organic layer was washed with water and saturated brine, and dried over anhydrous sodium sulfate. The solvent was then evaporated under reduced pressure. The residue was purified by preparative thin-layer chromatography (chloroform/methanol=98/2) to give 7-chloro-2-isopropylimidazo[1,2-c]pyrimidine (64.7 mg, yield 43%).

Workup

temperatureto cool to room temperature
filtrationthe mixture was filtered through Celite (registered trademark)
extractionextracted with ethyl acetate
washThe organic layer was washed with water and saturated brine
dry with materialdried over anhydrous sodium sulfate
customThe solvent was then evaporated under reduced pressure
customThe residue was purified by preparative thin-layer chromatography (chloroform/methanol=98/2)

Sources & evidence

ORD record: ord-60ecab20417143f8a321522b7f8bea52
Source dataset: uspto-grants-2015_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09000186B2

Reaction notes

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