Triphenylphosphine → Tert-butyl 2-[4-(2-aminopyrimidin-5-yl)-2-fluorophenoxy]propionate

HRID 500151Notes

Reaction equation

HRID 500151 reaction equation
C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N(C(OCC)=O)=NC(OCC)=O.[OH:32][C@@H:33]([CH3:41])[C:34]([O:36][C:37]([CH3:40])([CH3:39])[CH3:38])=[O:35].[NH2:42][C:43]1[N:48]=[CH:47][C:46]([C:49]2[CH:54]=[CH:53][C:52](O)=[C:51]([F:56])[CH:50]=2)=[CH:45][N:44]=1>O1CCCC1>[NH2:42][C:43]1[N:48]=[CH:47][C:46]([C:49]2[CH:54]=[CH:53][C:52]([O:32][CH:33]([CH3:41])[C:34]([O:36][C:37]([CH3:40])([CH3:39])[CH3:38])=[O:35])=[C:51]([F:56])[CH:50]=2)=[CH:45][N:44]=1

Participants

6

Reactant 4

HCID 11776TriphenylphosphineHCID 220568ethyl N-ethoxycarbonyliminocarbamateHCID 129438461,1-Dimethylethyl (2S)-2-hydroxypropanoateHCID 672239574-(2-Aminopyrimidin-5-yl)-2-fluorophenol

Product 1

HCID 67223953Tert-butyl 2-[4-(2-aminopyrimidin-5-yl)-2-fluorophenoxy]propionateYield 72%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of triphenylphosphine (0.315 g, 1.2 mmol) in tetrahydrofuran (THF, 5.0 mL) was added diethyl azodicarboxylate (0.19 mL, 1.2 mmol) and tert-butyl(S)-2-hydroxypropanoate (292 mg, 2 mmol) followed by 4-(2-aminopyrimidin-5-yl)-2-fluorophenol (0.20 g, 1.0 mmol) at RT (RT) under nitrogen. The mixture was stirred overnight at RT, evaporated and the residue was purified by chromatography on silica gel to afford the desired product (0.24 g, 72%). LCMS: (M+H)=334. 1.

Workup

  1. custom(RT)
  2. customevaporated
  3. customthe residue was purified by chromatography on silica gel

Sources & evidence

ORD record
ord-1d771913e51a4000b228ef7ef2ffbe09
Source dataset
uspto-grants-2010_08
Patent number
US07767675B2

Reaction notes

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