Triphenylphosphine → 2-Chloro-5-(cyclopropylmethoxy)pyrimidine

HRID 2277326Notes

Reaction equation

HRID 2277326 reaction equation
[CH:1]1([CH2:4][OH:5])[CH2:3][CH2:2]1.[Cl:6][C:7]1[N:12]=[CH:11][C:10](O)=[CH:9][N:8]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(C)C=CC=CC=1.N(C(OC(C)C)=O)=NC(OC(C)C)=O>C1(C)C=CC=CC=1>[Cl:6][C:7]1[N:12]=[CH:11][C:10]([O:5][CH2:4][CH:1]2[CH2:3][CH2:2]2)=[CH:9][N:8]=1

Participants

6

Reactant 4

HCID 11776TriphenylphosphineHCID 75644CyclopropanemethanolHCID 145957002-Chloro-5-pyrimidinolHCID 66880968DIAD toluene

Product 1

HCID 534406182-Chloro-5-(cyclopropylmethoxy)pyrimidineYield 93.3%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

To a solution of cyclopropylmethanol (276 mg), 2-chloropyrimidin-5-ol (500 mg) and triphenylphosphine (1.51 g) in toluene (20 mL) was added dropwise diisopropyl azodicarboxylate toluene solution (1.9 M, 3 mL), and the mixture was stirred at room temperature overnight. The reaction mixture was concentrated under reduced pressure, and the residue was purified by silica gel column chromatography (hexane/ethyl acetate) to give the title compound (659 mg). 1H NMR (300 MHz, DMSO-d6) δ 0.21-0.49 (2H, m), 0.49-0.69 (2H, m), 1.07-1.46 (1H, m), 4.00 (2H, d, J=7.2 Hz), 8.53 (2H, s).

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. customthe residue was purified by silica gel column chromatography (hexane/ethyl acetate)

Sources & evidence

ORD record
ord-3daddb9dee2742fbbec7bdb7bba2a093
Source dataset
uspto-grants-2015_09
Patent number
US09133129B2

Reaction notes

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