Triphenylphosphine → HCID 58174058, compound

HRID 339805Notes

Reaction equation

HRID 339805 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-5f73058f0fc949629bbef0cc2d53319d
Source dataset
uspto-grants-2014_11
Patent number
US08895568B2

Reaction notes

Loading…