Pyridine → HCID 58174070, compound

HRID 339800Notes

Reaction equation

HRID 339800 reaction equation
[N:1]1[C:10]2[C:5](=[N:6][CH:7]=[CH:8][N:9]=2)[C:4]([NH:11][CH2:12][CH2:13][C:14]2[CH:19]=[CH:18][C:17]([OH:20])=[CH:16][CH:15]=2)=[N:3][CH:2]=1.[CH:21]([C:24]1[CH:29]=[CH:28][C:27](B(O)O)=[CH:26][CH:25]=1)([CH3:23])[CH3:22].N1C=CC=CC=1>C(Cl)Cl.CC([O-])=O.CC([O-])=O.[Cu+2]>[CH:21]([C:24]1[CH:29]=[CH:28][C:27]([O:20][C:17]2[CH:18]=[CH:19][C:14]([CH2:13][CH2:12][NH:11][C:4]3[C:5]4[C:10](=[N:9][CH:8]=[CH:7][N:6]=4)[N:1]=[CH:2][N:3]=3)=[CH:15][CH:16]=2)=[CH:26][CH:25]=1)([CH3:23])[CH3:22]

Participants

6

Reactant 3

HCID 1049PyridineHCID 27734804-Isopropylphenylboronic acidHCID 58174068HCID 58174068, compound

Product 1

HCID 58174070HCID 58174070, compoundYield 11%

Reagents, catalysts & solvents 2

HCID 8895Cupric acetateCatalystHCID 6344DichloromethaneSolvent

Procedure

4-[2-(Pteridin-4-ylamino)-ethyl]-phenol (500 mg, 1.9 mmol), 4-isopropylphenylboronic acid (400 mg, 2.4 mmol), anh. Cu(OAc)2 (360 mg, 2.0 mmol) and powdered, freshly activated 4 Å molecular sieves (approximately 1 g) were combined in CH2Cl2 (15 mL), treated with pyridine (920 μL, 900 mg, 11.4 mmol) and sealed and stirred for 20 h with a moisture trap. The reaction was suction filtered and the filtrate shaken with dilute aqueous NH4OH. The organic phase was washed with H2O and brine and concentrated in vacuo. The residue was purified by preparative RP-HPLC using 80% MeCN/H2O to yield {2-[4-(4-isopropylphenoxy)-phenyl]-ethyl}-pteridin-4-yl-amine (78 mg, 11%) as a tan solid: mp 105-106.5° C.

Workup

  1. customsealed
  2. filtrationfiltered
  3. stirringthe filtrate shaken with dilute aqueous NH4OH
  4. washThe organic phase was washed with H2O and brine
  5. concentrationconcentrated in vacuo
  6. customThe residue was purified by preparative RP-HPLC

Sources & evidence

ORD record
ord-35a82d84932e41819c2f5989db0d3b28
Source dataset
uspto-grants-2014_11
Patent number
US08895568B2

Reaction notes

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