Triphenylphosphine → 5-[2-(tert-Butyl-dimethyl-silanyloxy)-2-cyclopropyl-ethoxy]-2,4,6-trichloro-pyrimidine

HRID 528490Notes

Reaction equation

HRID 528490 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]([Si:15]([CH3:24])([CH3:23])[O:16][CH:17]([CH:20]1[CH2:22][CH2:21]1)[CH2:18]O)([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>C1COCC1>[C:11]([Si:15]([CH3:24])([CH3:23])[O:16][CH:17]([CH:20]1[CH2:22][CH2:21]1)[CH2:18][O:9][C:5]1[C:4]([Cl:10])=[N:3][C:2]([Cl:1])=[N:7][C:6]=1[Cl:8])([CH3:14])([CH3:13])[CH3:12]

Participants

6

Reactant 4

HCID 11776TriphenylphosphineHCID 5363146Diisopropyl azodicarboxylateHCID 866673322,4,6-Trichloropyrimidin-5-olHCID 867117632-(tert-Butyl-dimethyl-silanyloxy)-2-cyclopropyl-ethanol

Product 1

HCID 867117655-[2-(tert-Butyl-dimethyl-silanyloxy)-2-cyclopropyl-ethoxy]-2,4,6-trichloro-pyrimidineYield 83%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 2,4,6-trichloro-pyrimidin-5-ol (250 mg, 1.25 mmol), 2-(tert-butyl-dimethyl-silanyloxy)-2-cyclopropyl-ethanol (407 mg, 1.88 mmol) and triphenylphosphine (493 mg, 1.88 mmol) in THF (12 mL) was added DIAD (370 μL, 1.88 mmol). The reaction mixture was stirred at RT for 18 hours before being concentrated in vacuo. The resultant residue was purified by column chromatography (SiO2, gradient 0-30% ethyl acetate in cyclohexane) to give 5-[2-(tert-Butyl-dimethyl-silanyloxy)-2-cyclopropyl-ethoxy]-2,4,6-trichloro-pyrimidine as a viscous yellow oil (411 mg, 83%). 1H NMR (400 MHz, CDCl3): δ 4.14 (1H, dd, J=8.83, 6.02 Hz), 3.99 (1H, dd, J=8.82, 4.21 Hz), 3.60-3.53 (1H, m), 1.13-1.03 (1H, m), 0.89 (9H, s), 0.56-0.50 (2H, m), 0.46-0.28 (2H, m), 0.10 (3H, s), 0.07 (3H, s).

Workup

  1. concentrationbefore being concentrated in vacuo
  2. customThe resultant residue was purified by column chromatography (SiO2, gradient 0-30% ethyl acetate in cyclohexane)

Sources & evidence

ORD record
ord-34929c7fd3e144f498c82af76d414980
Source dataset
uspto-grants-2016_05
Patent number
US09346817B2

Reaction notes

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