Water → HCID 57708304, compound

HRID 404824Notes

Reaction equation

HRID 404824 reaction equation
[O:1]1[CH2:6][CH2:5][O:4][C:3]2[CH:7]=[C:8]([OH:11])[CH:9]=[CH:10][C:2]1=2.C([O-])([O-])=O.[Cs+].[Cs+].Cl[C:19]1[N:24]=[CH:23][N:22]=[C:21]([NH:25][C:26]2[CH:31]=[CH:30][CH:29]=[C:28]([NH2:32])[N:27]=2)[CH:20]=1.O>CN1C(=O)CCC1.[Cu]I>[O:1]1[CH2:6][CH2:5][O:4][C:3]2[CH:7]=[C:8]([O:11][C:19]3[N:24]=[CH:23][N:22]=[C:21]([NH:25][C:26]4[CH:31]=[CH:30][CH:29]=[C:28]([NH2:32])[N:27]=4)[CH:20]=3)[CH:9]=[CH:10][C:2]1=2

Participants

7

Reactant 4

HCID 962WaterHCID 10796Cesium carbonateHCID 91152732,3-Dihydro-1,4-benzodioxin-6-olHCID 57708264N2-(6-chloropyrimidin-4-yl)pyridine-2,6-diamine

Product 1

HCID 57708304HCID 57708304, compoundYield 29%

Reagents, catalysts & solvents 2

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 13387N-methyl-2-pyrrolidoneSolvent

Conditions

Temperature
100 °C

Procedure

A stirred mixture of 2,3-dihydrobenzo[b][1,4]dioxin-6-ol (0.137 g, 0.90 mmol), Cs2CO3 (0.734 g, 2.25 mmol), CuI (0.02 g, 10% w/w), and N2-(6-chloropyrimidin-4-yl)pyridine-2,6-diamine (0.29 g, 0.90 mmol) in NMP (1 mL) was heated at 100° C. for 16 h. The reaction mixture was cooled to rt and slowly added to demineralised water. The solid that precipitated was collected by filtration and was further purified by column chromatography (SiO2, 60-120, pet ether/ethyl acetate, 7/3) to give N2-(6-(2,3-dihydrobenzo[b][1,4]dioxin-6-yloxy)pyrimidin-4-yl)pyridine-2,6-diamine (0.088 g, 29%) as yellow solid.

Workup

  1. temperatureThe reaction mixture was cooled to rt
  2. customThe solid that precipitated
  3. filtrationwas collected by filtration
  4. customwas further purified by column chromatography (SiO2, 60-120, pet ether/ethyl acetate, 7/3)

Sources & evidence

ORD record
ord-de91d0e38ff247608c203e059b6904bb
Source dataset
uspto-grants-2014_06
Patent number
US08748606B2

Reaction notes

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