Dimethylformamide dimethyl acetal → N'-(3-Cyano-6-methyl-pyridin-2-yl)-N,N-dimethyl-formamidine

HRID 607158Notes

Reaction equation

HRID 607158 reaction equation
[NH2:1][C:2]1[N:9]=[C:8]([CH3:10])[CH:7]=[CH:6][C:3]=1[C:4]#[N:5].CO[CH:13](OC)[N:14]([CH3:16])[CH3:15]>C1(C)C=CC=CC=1>[C:4]([C:3]1[C:2]([N:1]=[CH:13][N:14]([CH3:16])[CH3:15])=[N:9][C:8]([CH3:10])=[CH:7][CH:6]=1)#[N:5]

Participants

4

Reactant 2

HCID 78373Dimethylformamide dimethyl acetalHCID 130271112-Amino-6-methylpyridine-3-carbonitrile

Product 1

HCID 66808573N'-(3-Cyano-6-methyl-pyridin-2-yl)-N,N-dimethyl-formamidineYield 98%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A solution of the product of Example 10A (10 g, 75.19 mmol) and N,N-Dimethylformamide dimethyl acetal (11 mL, 82.71 mmol) in toluene (100 mL) was heated at reflux for 6 hours. After cooling to room temperature, the solution was concentrated under vacuum to provide the title compound as a yellow solid (13.78 g, 98%). 1H NMR (300 MHz, DMSO-d6) δ ppm: 2.41 (s, 3H), 3.06 (s, 3H), 3.14 (s, 3H), 6.87 (d, J=7.7 Hz, 1H), 7.89 (d, J=8.1 Hz, 1H), 8.59 (s, 1H).

Workup

  1. temperatureat reflux for 6 hours
  2. concentrationthe solution was concentrated under vacuum

Sources & evidence

ORD record
ord-c8d660a72f9940808ef131416f32edb8
Source dataset
uspto-grants-2011_03
Patent number
US07915411B2

Reaction notes

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