Triphenylphosphine → HCID 58174058, compound

HRID 1255899Notes

Reaction equation

HRID 1255899 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.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[CH2:40]([O:47][C:48]1[CH:53]=[CH:52][C:51]([CH2:54][CH2:55]O)=[CH:50][CH:49]=1)[C:41]1[CH:46]=[CH:45][CH:44]=[CH:43][CH:42]=1.CC(OC(/N=N/C(OC(C)C)=O)=O)C>O1CCOCC1>[CH2:40]([O:47][C:48]1[CH:49]=[CH:50][C:51]([CH2:54][CH2:55][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:52][CH:53]=1)[C:41]1[CH:42]=[CH:43][CH:44]=[CH:45][CH:46]=1

Participants

6

Reactant 4

HCID 11776TriphenylphosphineHCID 3017260p-(Benzyloxy)phenethyl alcoholHCID 5363146Diisopropyl azodicarboxylateHCID 58174068HCID 58174068, compound

Product 1

HCID 58174058HCID 58174058, compoundYield 20%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

4-[2-(Pteridin-4-ylamino)-ethyl]-phenol (300 mg, 10.1 mmol), triphenylphosphine (790 mg, 3.0 mmol) and 2-(4-benzyloxyphenyl)ethanol (700 mg, 3.0 mmol) were combined in 10 mL anh. dioxane, treated with diisopropylazodicarboxylate (590 μL, 610 mg, 3.0 mmol) and stirred for 18 h. The volatiles were removed in vacuo and the residue was chromatographed on SiO2 with EtOAc (10% to 40%) in CH2Cl2 to obtain (2-{4-[2-(4-benzyloxyphenyl)-ethoxy]-phenyl}-ethyl)-pteridin-4-ylamine (105 mg; 20%) as a white solid: mp 120-122° C.; ESIMS m/z 478 ([M+H]+); 1H NMR (300 MHz, CDCl3) δ 9.23 (s, 1H), 8.96 (s, 1H), 8.80 (s, 1H), 6.8-7.5 (m, 13H), 4.1 (m, 2H), 3.90 (m, 2H), 3.01 (m, 4H).

Workup

  1. customThe volatiles were removed in vacuo
  2. customthe residue was chromatographed on SiO2 with EtOAc (10% to 40%) in CH2Cl2

Sources & evidence

ORD record
ord-a495e067096c4d43bf51bcfb96f5ca5f
Source dataset
uspto-grants-2013_06
Patent number
US08461164B2

Reaction notes

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