N,N,N',N'-Tetramethylmethanediamine → 2-[(dimethylamino)methyl]-3-hydroxy-6-methyl-1-(2,2,2-trifluoroethyl)pyridin-4(1H)-one

HRID 1519036Notes

Reaction equation

Cl.[OH:2][C:3]1[C:4](=[O:15])[CH:5]=[C:6]([CH3:14])[N:7]([CH2:9][C:10]([F:13])([F:12])[F:11])[CH:8]=1.[CH3:16][N:17]([CH3:22])[CH2:18]N(C)C>C(O)C>[CH3:16][N:17]([CH2:22][C:8]1[N:7]([CH2:9][C:10]([F:11])([F:12])[F:13])[C:6]([CH3:14])=[CH:5][C:4](=[O:15])[C:3]=1[OH:2])[CH3:18]

Participants

Conditions

Temperature: 80 °C

Procedure

5-Hydroxy-2-methyl-1-(2,2,2-trifluoroethyl)pyridin-4(1H)-one hydrochloride (415 mg, 1.7 mmol) was mixed with N,N,N′,N′-tetramethylmethanediamine (4 mL) in ethanol (10 mL) and heated at 80° C. for 21 hours. The reaction mixture was concentrated by rotary evaporator and the residue was triturated with water to give 2-[(dimethylamino)methyl]-3-hydroxy-6-methyl-1-(2,2,2-trifluoroethyl)pyridin-4(1H)-one (315 mg) as white solid. Yield=70%; 1H NMR (DMSO-D6+D2O, 90 MHz) δ (ppm): 6.20 (s, 1H), 5.15 (q, J=8.8 Hz, 2H), 4.69 (br. s, 2H) and 2.37 (s, 3H); MS m/z 265 [M+1]+.

Workup

concentrationThe reaction mixture was concentrated by rotary evaporator
customthe residue was triturated with water

Sources & evidence

ORD record: ord-9b9d0982f44248829fe9fbe1befdb52d
Source dataset: uspto-grants-2015_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09073865B2

Reaction notes

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