2-Amino-5-methylpyridine → HCID 178426513, compound

HRID 717557Notes

Reaction equation

C([Li])CCC.[CH3:6][C:7]1[CH:8]=[CH:9][C:10]([NH2:13])=[N:11][CH:12]=1.[Br:14][C:15]1[CH:16]=[N:17][CH:18]=[C:19]([CH:22]=1)[C:20]#[N:21]>O1CCCC1>[Br:14][C:15]1[CH:16]=[N:17][CH:18]=[C:19]([CH:22]=1)[C:20](=[NH:21])[NH:13][C:10]1[CH:9]=[CH:8][C:7]([CH3:6])=[CH:12][N:11]=1

Participants

Conditions

Temperature: -40 °C

Procedure

n-Butyllithium (1.6 M, 5.14 mL, 0.0081 mol) was added slowly at a temperature of −78° C. over a period of 5 min to a solution of 5-methylpyridin-2-amine (0.738 g, 0.0068 mol) in anhydrous tetrahydrofuran (40 mL). The reaction temperature was raised to −40° C. and the reaction mixture was stirred for 15 min. It was cooled to −78° C. and 5-bromonicotinonitrile (1.25 g, 0.0068 mol) in tetrahydrofuran (5 mL) was added. The reaction temperature was raised to RT and the reaction mixture was stirred for 3 h. The reaction mixture was quenched with a saturated aqueous ammonium chloride solution (25 mL) and extracted with ethyl acetate (2×50 mL). The combined organic layers were dried over sodium sulphate and concentrated under vacuum to afford the crude product, which was used directly on the next step. MS (M+1): 292.1.

Workup

temperatureIt was cooled to −78° C.
temperatureThe reaction temperature was raised to RT
stirringthe reaction mixture was stirred for 3 h
customThe reaction mixture was quenched with a saturated aqueous ammonium chloride solution (25 mL)
extractionextracted with ethyl acetate (2×50 mL)
dry with materialThe combined organic layers were dried over sodium sulphate
concentrationconcentrated under vacuum

Sources & evidence

ORD record: ord-560ebb2a790748ea86579cc27ad833bd
Source dataset: uspto-grants-2015_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09193724B2

Reaction notes

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