2,4,6-Trichloropyrimidine → HCID 117678390, compound

HRID 1778188Notes

Reaction equation

HRID 1778188 reaction equation
[Cl:1][C:2]1[N:7]=[C:6]([Cl:8])[CH:5]=[C:4](Cl)[N:3]=1.[CH:10]1([C:14]#[N:15])[CH2:13][CH2:12][CH2:11]1.C[Si]([N-][Si](C)(C)C)(C)C.[Li+]>C1COCC1>[Cl:1][C:2]1[N:3]=[C:4]([C:10]2([C:14]#[N:15])[CH2:13][CH2:12][CH2:11]2)[CH:5]=[C:6]([Cl:8])[N:7]=1

Participants

5

Reactant 3

HCID 773782,4,6-TrichloropyrimidineHCID 78148CyanocyclobutaneHCID 2733832Lithium Hexamethyldisilazide

Product 1

HCID 117678390HCID 117678390, compoundYield 12%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a stirring solution of 2,4,6-trichloropyrimidine (1.00 g, 5.45 mmol) and cyclobutanecarbonitrile (0.53 mL, 5.5 mmol) in anhydrous THF (27 mL) at −78° C. and under nitrogen was added lithium bis(trimethylsilyl)amide (6.0 mL, 6.0 mmol, 1.0 M solution in THF) over 3 min. The cooling bath was removed after 5 further min, and stirring continued for 3 h. The reaction was quenched by the addition of sat. aq. NH4Cl, extracted with CH2Cl2 and organics dried over MgSO4. Following concentration, the reaction residue was purified by flash column chromatography (100:0 heptanes/EtOAc-85:15 heptanes/EtOAc) to afford the title compound as a colorless solid (0.147 g, 12%); 1H NMR (400 MHz, CDCl3) δ 7.54 (s, 1H), 2.97-2.82 (m, 2H), 2.82-2.67 (m, 2H), 2.51-2.35 (m, 1H), 2.35-2.16 (m, 1H).

Workup

  1. customThe cooling bath was removed after 5 further min
  2. customThe reaction was quenched by the addition of sat. aq. NH4Cl
  3. extractionextracted with CH2Cl2
  4. dry with materialorganics dried over MgSO4
  5. concentrationconcentration
  6. customthe reaction residue was purified by flash column chromatography (100:0 heptanes/EtOAc-85:15 heptanes/EtOAc)

Sources & evidence

ORD record
ord-fb86dd1c8627457f9b1ce4efa0c2d60a
Source dataset
uspto-grants-2016_02
Patent number
US09266862B2

Reaction notes

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