2-tert-Butyloxirane → HCID 86711759, compound

HRID 528477Notes

Reaction equation

HRID 528477 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]([CH:15]1[CH2:17][O:16]1)([CH3:14])([CH3:13])[CH3:12]>>[CH3:12][C:11]([CH3:14])([CH3:13])[CH:15]([OH:16])[CH2:17][O:9][C:5]1[C:4]([Cl:10])=[N:3][C:2]([Cl:1])=[N:7][C:6]=1[Cl:8]

Participants

3

Reactant 2

HCID 921742-tert-ButyloxiraneHCID 866673322,4,6-Trichloropyrimidin-5-ol

Product 1

HCID 86711759HCID 86711759, compoundYield 52%

Conditions

Temperature
100 °C

Procedure

A mixture of 2,4,6-trichloro-pyrimidin-5-ol (400 mg, 2.01 mmol) and 2-tert-butyl oxirane (3 mL) was heated at 100° C. for 3 hours before being cooled and concentrated in vacuo. The resultant residue was triturated in hot methanol and the insoluble material removed. The filtrate was concentrated in vacuo and the resultant residue was purified by column chromatography (SiO2, 0-15% ethyl acetate in cyclohexane) to give 3,3-Dimethyl-1-(2,4,6-trichloro-pyrimidin-5-yloxy)-butan-2-ol as a white solid (275 mg, 52%). 1H NMR (400 MHz, CDCl3): δ 4.28 (1H, dd, J=9.38, 2.19 Hz), 4.00 (1H, t, J=9.19 Hz), 3.76-3.69 (1H, m), 2.53 (1H, d, J=3.48 Hz), 0.95 (9H, s).

Workup

  1. temperaturebefore being cooled
  2. concentrationconcentrated in vacuo
  3. customThe resultant residue was triturated in hot methanol
  4. customthe insoluble material removed
  5. concentrationThe filtrate was concentrated in vacuo
  6. customthe resultant residue was purified by column chromatography (SiO2, 0-15% ethyl acetate in cyclohexane)

Sources & evidence

ORD record
ord-2d53566aaa9845d286990760446641f1
Source dataset
uspto-grants-2016_05
Patent number
US09346817B2

Reaction notes

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