Tributylstannane → 2-(Tributylstannyl)pyrimidine

HRID 1443872Notes

Reaction equation

HRID 1443872 reaction equation
[CH2:1]([SnH:5]([CH2:10][CH2:11][CH2:12][CH3:13])[CH2:6][CH2:7][CH2:8][CH3:9])[CH2:2][CH2:3][CH3:4].[Li+].CC([N-]C(C)C)C.[CH2:22]([Sn:26]([Li:35])([CH2:31][CH2:32][CH2:33][CH3:34])[CH2:27][CH2:28][CH2:29][CH3:30])[CH2:23][CH2:24][CH3:25].Br[C:37]1[N:42]=[CH:41][CH:40]=[CH:39][N:38]=1>C1COCC1>[CH2:22]([Sn:26]([Li:35])([CH2:27][CH2:28][CH2:29][CH3:30])[CH2:31][CH2:32][CH2:33][CH3:34])[CH2:23][CH2:24][CH3:25].[CH2:10]([Sn:5]([CH2:1][CH2:2][CH2:3][CH3:4])([CH2:6][CH2:7][CH2:8][CH3:9])[C:37]1[N:42]=[CH:41][CH:40]=[CH:39][N:38]=1)[CH2:11][CH2:12][CH3:13]

Participants

7

Reactant 4

HCID 5948TributylstannaneHCID 783452-BromopyrimidineHCID 2724682Lithium diisopropylamideHCID 178506970HCID 178506970, compound

Product 2

HCID 27632512-(Tributylstannyl)pyrimidineHCID 178506970HCID 178506970, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

(Example of the general procedure Tin-03, below) Tri-n-butylstannyl lithium was prepared at 0° C. in dry THF (20 mL) from tri-butyltin hydride (2.2 mL) and LDA (lithium diisopropylamide, 2M, 4.09 mL). The tri-n-butylstannyl lithium solution was then cooled to −78° C. and to it was added 2-bromopyrimidine (1 g). The reaction mixture was then allowed to warm up to room temperature over 8 hours. The reaction was then quenched with aqueous ammonium chloride solution. The organic layer was separated, and aqueous layer was extracted with ethyl acetate (3×20 mL). The combined organic layer was dried over magnesium sulfate, filtered and the filtrate concentrated in vacuo. The residue was purified by silica gel chromatography to afford 2-(tri-n-butylstannyl)-pyrimidine (190 mg).

Workup

  1. customThe reaction was then quenched with aqueous ammonium chloride solution
  2. customThe organic layer was separated
  3. extractionaqueous layer was extracted with ethyl acetate (3×20 mL)
  4. dry with materialThe combined organic layer was dried over magnesium sulfate
  5. filtrationfiltered
  6. concentrationthe filtrate concentrated in vacuo
  7. customThe residue was purified by silica gel chromatography

Sources & evidence

ORD record
ord-78828f4f87e24b0aaef97a830e5923d3
Source dataset
uspto-grants-2010_02
Patent number
US07662823B2

Reaction notes

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