2-Amino-5-methylpyridine → HCID 58178863, compound

HRID 1042015Notes

Reaction equation

HRID 1042015 reaction equation
[CH3:1][C:2]1[CH:3]=[CH:4][C:5]([NH2:8])=[N:6][CH:7]=1.[F:9][C:10]1[CH:17]=[CH:16][C:13]([CH:14]=O)=[CH:12][CH:11]=1.[N+:18](C(C)(C)C)#[C-:19]>CO>[F:9][C:10]1[CH:17]=[CH:16][C:13]([C:14]2[N:8]=[C:5]3[CH:4]=[CH:3][C:2]([CH3:1])=[CH:7][N:6]3[C:19]=2[NH2:18])=[CH:12][CH:11]=1

Participants

5

Reactant 3

HCID 153482-Amino-5-methylpyridineHCID 23577Tert-Butyl isocyanideHCID 680234-Fluorobenzaldehyde

Product 1

HCID 58178863HCID 58178863, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

To a stirred solution of 5-methylpyridin-2-amine (260 mg, 2.4 mmol) in 20 mL of MeOH was added 4-fluorobenzaldehyde (0.26 mL, 2.40 mmol), and followed by 1.0 N HClO4 in MeOH (0.20 mL, 0.20 mmol). The reaction mixture was stirred at room temperature for 0.5 hour which was followed by addition of 2-isocyano-2-methylpropane (0.23 mL, 2.0 mmol). The stirring was continued at room temperature overnight. HPLC/MS test showed that the desired product Reference Compound 76-1 was a major peak.

Workup

  1. waitThe stirring was continued at room temperature overnight

Sources & evidence

ORD record
ord-9c40340536954a5eac33b9c118a47f76
Source dataset
uspto-grants-2013_10
Patent number
US08557801B2

Reaction notes

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