Triphenylphosphine → HCID 86711734, compound

HRID 528447Notes

Reaction equation

HRID 528447 reaction equation
[Cl:1][C:2]1[N:7]=[C:6]([Cl:8])[C:5]([OH:9])=[C:4]([Cl:10])[N:3]=1.C([CH:13](O)[C:14]([O-:16])=[O:15])C.[C:18]1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=C[CH:19]=1.CC(OC(/N=N/C(OC(C)C)=O)=O)C>O1CCOCC1>[CH2:18]([O:16][C:14](=[O:15])[CH2:13][O:9][C:5]1[C:4]([Cl:10])=[N:3][C:2]([Cl:1])=[N:7][C:6]=1[Cl:8])[CH3:19]

Participants

6

Reactant 4

HCID 11776TriphenylphosphineHCID 4071895Alpha-HydroxybutyrateHCID 5363146Diisopropyl azodicarboxylateHCID 866673322,4,6-Trichloropyrimidin-5-ol

Product 1

HCID 86711734HCID 86711734, compoundYield 62.3%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

A mixture of 2,4,6-trichloro-pyrimidin-5-ol (3.0 g, 15.0 mmol), ethylglycolate (16.7 mL, 17.3 mmol), triphenylphosphine (4.5 g, 17.3 mmol) and DIAD (3.4 mL, 17.3 mmol) in dioxane (100 mL) was stirred at RT for 18 hours then concentrated in vacuo. The resulting residue was purified by column chromatography (SiO2, gradient 0-15% ethyl acetate in cyclohexane) affording (2,4,6-Trichloro-pyrimidin-5-yloxy)-acetic acid ethyl ester as a white solid (2.67 g, 62%). 1H NMR (400 MHz, CDCl3): δ 4.77 (2H, s), 4.28 (2H, q, J=7.14 Hz), 1.32 (3H, t, J=7.15 Hz).

Workup

  1. concentrationthen concentrated in vacuo
  2. customThe resulting residue was purified by column chromatography (SiO2, gradient 0-15% ethyl acetate in cyclohexane)

Sources & evidence

ORD record
ord-e3ad15d2d9874199aa1fbd02a0cb7e90
Source dataset
uspto-grants-2016_05
Patent number
US09346817B2

Reaction notes

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