6-tert-Butylpyridin-2-amine → HCID 86689751, compound

HRID 1396396Notes

Reaction equation

HRID 1396396 reaction equation
Cl[C:2]1[CH:7]=[C:6]([Cl:8])[N:5]=[N:4][C:3]=1[C:9]([O:11][CH3:12])=[O:10].[C:13]([C:17]1[N:22]=[C:21]([NH2:23])[CH:20]=[CH:19][CH:18]=1)([CH3:16])([CH3:15])[CH3:14]>C(#N)C>[C:13]([C:17]1[N:22]=[C:21]([NH:23][C:2]2[CH:7]=[C:6]([Cl:8])[N:5]=[N:4][C:3]=2[C:9]([O:11][CH3:12])=[O:10])[CH:20]=[CH:19][CH:18]=1)([CH3:16])([CH3:14])[CH3:15]

Participants

4

Reactant 2

HCID 134946346-tert-Butylpyridin-2-amineHCID 17848322Methyl 4,6-dichloropyridazine-3-carboxylate

Product 1

HCID 86689751HCID 86689751, compoundYield 35%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
130 °C

Procedure

A mixture of methyl 4,6-dichloropyridazine-3-carboxylate (0.69 g, 3.33 mmol) and 6-tert-butylpyridin-2-amine (1.00 g, 6.67 mmol) was dissolved in acetonitrile (3 mL) and heated at 130° C. for 14 h The dark brown mixture was cooled, concentrated onto silica, and purified by chromatography (silica, 80 g, 0-20% acetone in dichloromethane, 40 min) to give methyl 4-(6-tert-butylpyridin-2-ylamino)-6-chloropyridazine-3-carboxylate (372 mg, 1.16 mmol, 35%) as a yellow solid. MS (EI/CI) m/z: 321.0 [M+H].

Workup

  1. temperaturewas cooled
  2. concentrationconcentrated onto silica
  3. custompurified by chromatography (silica, 80 g, 0-20% acetone in dichloromethane, 40 min)

Sources & evidence

ORD record
ord-a3f76bc6012e426db5adbca68780334d
Source dataset
uspto-grants-2014_12
Patent number
US08901124B2

Reaction notes

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