Triphenylphosphine → HCID 86711768, compound

HRID 528495Notes

Reaction equation

HRID 528495 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:11]([O:15][C:16](=[O:22])[N:17]([CH2:19][CH2:20]O)[CH3:18])([CH3:14])([CH3:13])[CH3:12].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.CC(OC(/N=N/C(OC(C)C)=O)=O)C>O1CCOCC1>[C:11]([O:15][C:16](=[O:22])[N:17]([CH3:18])[CH2:19][CH2:20][O:9][C:5]1[C:4]([Cl:10])=[N:3][C:2]([Cl:1])=[N:7][C:6]=1[Cl:8])([CH3:13])([CH3:14])[CH3:12]

Participants

6

Reactant 4

HCID 11776TriphenylphosphineHCID 545700N-(tert-Butoxycarbonyl)-N-methyl-2-aminoethanolHCID 5363146Diisopropyl azodicarboxylateHCID 866673322,4,6-Trichloropyrimidin-5-ol

Product 1

HCID 86711768HCID 86711768, compoundYield 124.5%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

A mixture of 2,4,6-trichloro-pyrimidin-5-ol (300 mg, 1.50 mmol), (2-hydroxy-ethyl)-methyl-carbamic acid tert-butyl ester (300 mg, 1.71 mmol), triphenylphosphine (455 mg, 1.73 mmol) and DIAD (339 μL, 1.73 mmol) in dioxane (2.5 mL) was stirred at RT for 1.5 hours then concentrated in vacuo. The resulting residue was purified by column chromatography (SiO2, gradient 0-50% ethyl acetate in cyclohexane) affording Methyl-[2-(2,4,6-trichloro-pyrimidin-5-yloxy)-ethyl]-carbamic acid tert-butyl ester (666 mg, quantitative). LCMS: RT=3.09 min, [M-Boc+Na]+=279.

Workup

  1. concentrationthen concentrated in vacuo
  2. customThe resulting residue was purified by column chromatography (SiO2, gradient 0-50% ethyl acetate in cyclohexane)

Sources & evidence

ORD record
ord-64c81e2704e340908a00980301f7aa4a
Source dataset
uspto-grants-2016_05
Patent number
US09346817B2

Reaction notes

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