4-Aminopyridine → 1-(Pyridin-4-yl)-3-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)urea

HRID 1771539Notes

Reaction equation

HRID 1771539 reaction equation
[N:1]([C:4]1[CH:9]=[CH:8][C:7]([B:10]2[O:14][C:13]([CH3:16])([CH3:15])[C:12]([CH3:18])([CH3:17])[O:11]2)=[CH:6][CH:5]=1)=[C:2]=[O:3].[N:19]1[CH:24]=[CH:23][C:22]([NH2:25])=[CH:21][CH:20]=1.C(N(CC)CC)C>C1COCC1>[N:19]1[CH:24]=[CH:23][C:22]([NH:25][C:2]([NH:1][C:4]2[CH:9]=[CH:8][C:7]([B:10]3[O:14][C:13]([CH3:16])([CH3:15])[C:12]([CH3:18])([CH3:17])[O:11]3)=[CH:6][CH:5]=2)=[O:3])=[CH:21][CH:20]=1

Participants

5

Reactant 3

HCID 17274-AminopyridineHCID 8471TriethylamineHCID 27734742-(4-Isocyanatophenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane

Product 1

HCID 666878001-(Pyridin-4-yl)-3-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)urea

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

2-(4-isocyanatophenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (1 g, 4.1 mmol) was dissolved in dry THF and stirred with pyridin-4-amine (460 mg, 4.9 mmol) and triethlyamine (1.13 ml, 8.2 mmol) at 60° C. for 3 hours. The mixture was cooled and then purified by flash chromatography (0-100% EtOAc in Petroleum ether 40-60, followed by 0-10% MeOH in EtOAc) to afford the title compound. (875 mg, 63%) uPLC (method D), (M+H+) 340, Rt=0.89 mins

Workup

  1. temperatureThe mixture was cooled
  2. custompurified by flash chromatography (0-100% EtOAc in Petroleum ether 40-60, followed by 0-10% MeOH in EtOAc)

Sources & evidence

ORD record
ord-131b0602caec4009909d4a950b3fb588
Source dataset
uspto-grants-2016_02
Patent number
US09249129B2

Reaction notes

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