2,6-Lutidine → HCID 178433431, compound

HRID 359682Notes

Reaction equation

HRID 359682 reaction equation
[Br:1][C:2]1[C:3]([OH:10])=[N:4][C:5]([CH3:9])=[N:6][C:7]=1Cl.[C:11]([C:13]1[CH:14]=[C:15]([CH2:19][NH2:20])[CH:16]=[N:17][CH:18]=1)#[N:12].N1C(C)=CC=CC=1C>COCCOC>[Br:1][C:2]1[C:3](=[O:10])[N:4]=[C:5]([CH3:9])[NH:6][C:7]=1[NH:12][CH2:11][C:13]1[CH:14]=[C:15]([C:19]#[N:20])[CH:16]=[N:17][CH:18]=1

Participants

5

Reactant 3

HCID 79372,6-LutidineHCID 200639425-(Aminomethyl)-3-pyridinecarbonitrileHCID 1784334305-bromo-6-chloro-2-methyl-1H-pyrimidin-4-one

Product 1

HCID 178433431HCID 178433431, compoundYield 31%

Reagents, catalysts & solvents 1

HCID 80711,2-DimethoxyethaneSolvent

Conditions

Temperature
90 °C

Procedure

A stirred suspension of 5-bromo-6-chloro-2-methyl-4-pyrimidinol (1.57 g, 7.04 mmol), 5-cyano-3-aminomethylpyridine (1.03 g, 7.74 mmol), and 2,6-lutidine (2.00 mL, 17.4 mmol) in 1,2-dimethoxyethane (7.0 mL) was heated at 90° C. for 15 hours. Solvent was removed in vacuo, and the residue was suspended in water. The white precipitate was isolated by filtration with aqueous rinse, and then recrystallized from methanol/diethyl ether to afford crude product (922 mg, 41%). The crude product was adsorbed onto silica gel. The product was eluted with 4:1 ethyl acetate:hexane (150 mL) followed by methanol (300 mL). The methanol eluant was concentrated in vacuo, and the residue was recrystallized from methanol/diethyl ether to give the title compound in analytically pure form (705 mg, 2.20 mmol, 31% yield): mp 260.0°-260.5° C.; Rf 0.51 (20% MeOH in EtOAc); 1H NMR (DMSO-D6, 400 MHz)δ11.0 (s, 1H), 8.88 (d, J=1.69 Hz, 1H), 8.77 (d, J=1.64 Hz, 1H), 8.16 (s, 1H), 7.34 (t, J=6.14 Hz, 1H), 4.60 (d, J=6.00 Hz, 2H), 2.16 (s, 3H); IR (KBr) 3280 (NH), 2620-3000 (CH), 2230 (CN), 1645, 1605, 1585 (C=C, C=N); UV (MeOH)λ275.5 (ε10900).

Workup

  1. customSolvent was removed in vacuo
  2. customThe white precipitate was isolated by filtration with aqueous rinse
  3. customrecrystallized from methanol/diethyl ether
  4. customto afford crude product (922 mg, 41%)
  5. washThe product was eluted with 4:1 ethyl acetate
  6. concentrationThe methanol eluant was concentrated in vacuo
  7. customthe residue was recrystallized from methanol/diethyl ether

Sources & evidence

ORD record
ord-9bff47f5dfda487d9806241b435ec1da
Source dataset
uspto-grants-1991_03
Patent number
US05002949

Reaction notes

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