Pyridine → HCID 53477163, compound

HRID 576814Notes

Reaction equation

HRID 576814 reaction equation
[CH:1]1([C:4]2[N:9]=[C:8]([CH3:10])[C:7]([C:11]([OH:13])=O)=[CH:6][N:5]=2)[CH2:3][CH2:2]1.CN[C:16]1[N:17]=[N:18][CH:19]=[CH:20][CH:21]=1.[N:22]1C=CC=C[CH:23]=1.ClCCl.CO>ClCCl>[N:17]1[CH:16]=[CH:21][C:20]([N:22]([CH3:23])[C:11]([C:7]2[C:8]([CH3:10])=[N:9][C:4]([CH:1]3[CH2:2][CH2:3]3)=[N:5][CH:6]=2)=[O:13])=[CH:19][N:18]=1

Participants

6

Reactant 4

HCID 1049PyridineHCID 19831906N-Methylpyridazin-3-aMineHCID 21226129Dichloromethane methanolHCID 223084932-Cyclopropyl-4-methylpyrimidine-5-carboxylic acid

Product 1

HCID 53477163HCID 53477163, compoundYield 39%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent3×

Procedure

2-Cyclopropyl-4-methyl-pyrimidine-5-carboxylic acid (200 mg, 1.12 mmol) was dissolved in anhydrous dichloromethane (20 ml). 4-N,N-Dimethylaminopyridine (23 mg, 0.2 mmol) and N,N-diisopropyl carbodiimide (0.17 ml, 1.12 mmol) were sequentially added and the reaction mixture was stirred at room temperature for 2 hours. Ak methylaminopyridazine (147 mg, 1.35 mmol) was dissolved in anhydrous dichloromethane (5 ml) and together with pyridine (0.35 ml, 1.12 mmol) added to the reaction mixture. Stirring at room temperature was continued for 15 hours. The progress of the reaction was monitored by thin layer chromatography (dichloromethane/methanol 9:1). The reaction mixture was diluted with dichloromethane (50 ml), washed two times with distilled water (5 ml each). The organic phase was dried over sodium sulfate and the organic solvent was evaporated in vacuo. The crude product was purified by flash chromatography (dichloromethane/methanol, gradient: 100/0 to 90/10 (v/v), duration: 50 min). The title compound was isolated as a brownish oil (119 mg, yield: 39%, purity: 95%).

Workup

  1. additionadded to the reaction mixture
  2. stirringStirring at room temperature
  3. waitwas continued for 15 hours
  4. washwashed two times with distilled water (5 ml each)
  5. dry with materialThe organic phase was dried over sodium sulfate
  6. customthe organic solvent was evaporated in vacuo
  7. customThe crude product was purified by flash chromatography (dichloromethane/methanol, gradient: 100/0 to 90/10 (v/v), duration: 50 min)

Sources & evidence

ORD record
ord-14c4d53c31de4d75a6480c3000c0813b
Source dataset
uspto-grants-2015_05
Patent number
US09040537B2

Reaction notes

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