Lithium diisopropylamide → HCID 68799356, compound

HRID 2099572Notes

Reaction equation

HRID 2099572 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[C:3]([CH2:7][C:8]2[CH:9]=[N:10][CH:11]=[CH:12][CH:13]=2)[CH:2]=1.[Li+].CC([N-]C(C)C)C.Cl[CH:23]([C:32]1[CH:37]=[CH:36][N:35]=[C:34]([S:38][CH3:39])[N:33]=1)[C:24]1[CH:25]=[C:26]([CH:29]=[CH:30][CH:31]=1)[C:27]#[N:28]>C1COCC1>[CH3:39][S:38][C:34]1[N:33]=[C:32]([CH:23]([C:24]2[CH:25]=[C:26]([CH:29]=[CH:30][CH:31]=2)[C:27]#[N:28])[CH:7]([C:8]2[CH:9]=[N:10][CH:11]=[CH:12][CH:13]=2)[C:3]2[CH:2]=[N:1][CH:6]=[CH:5][CH:4]=2)[CH:37]=[CH:36][N:35]=1

Participants

5

Reactant 3

HCID 2724682Lithium diisopropylamideHCID 147626403,3'-MethylenedipyridineHCID 68801608HCID 68801608, compound

Product 1

HCID 68799356HCID 68799356, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To the solution of 3-(pyridin-3-ylmethyl)pyridine (1.24 g, 7.26 mmol) in THF (32 mL) at −78° C. was added LDA (4.4 mL, 1.8 M) and stirred for 1 h. 3-{chloro[2-(methylthio)pyrimidin-4-yl]methyl}benzonitrile (2.0 g, 7.25 mmol) in THF (5 mL) was added. The mixture was stirred at 0° C. for 2 h. The reaction was quenched with ice and extracted with CH2Cl2. The combined organic layer was dried, filtered, and concentrated to give a solid. The solid was purified by silica gel chromatography (3% MeOH in CH2Cl2) to give (±)-3-{1-[2-(methylthio)pyrimidin-4-yl]-2,2-dipyridin-3-ylethyl}benzonitrile. LRMS m/z (M+H) Calcd: 410.5, found: 410.1. Step D

Workup

  1. stirringThe mixture was stirred at 0° C. for 2 h
  2. customThe reaction was quenched with ice
  3. extractionextracted with CH2Cl2
  4. customThe combined organic layer was dried
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customto give a solid
  8. customThe solid was purified by silica gel chromatography (3% MeOH in CH2Cl2)

Sources & evidence

ORD record
ord-e1fbadd20dc6435289b448993a3eec41
Source dataset
uspto-grants-2009_08
Patent number
US07569589B2

Reaction notes

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