2-Chloropyrimidine → 2-(Tributylstannyl)pyrimidine

HRID 335509Notes

Reaction equation

[CH2:1]([Sn:5]([Li])([CH2:10][CH2:11][CH2:12][CH3:13])[CH2:6][CH2:7][CH2:8][CH3:9])[CH2:2][CH2:3][CH3:4].Cl[C:16]1[N:21]=[CH:20][CH:19]=[CH:18][N:17]=1>>[CH2:1]([Sn:5]([CH2:10][CH2:11][CH2:12][CH3:13])([CH2:6][CH2:7][CH2:8][CH3:9])[C:16]1[N:21]=[CH:20][CH:19]=[CH:18][N:17]=1)[CH2:2][CH2:3][CH3:4]

Participants

Reactant 2

HCID 744042-Chloropyrimidine

HCID 178506970HCID 178506970, compound

Product 1

HCID 27632512-(Tributylstannyl)pyrimidine

Procedure

Reaction of tri-n-butylstannyl lithium with 2-chloropyrimidine affords 2-(tributylstannyl)pyrimidine which can be condensed the an acid chloride such as 5 under palladium catalysis to afford these desired ketones.

Sources & evidence

ORD record: ord-cbc87f6b7a6f4f01963d7ecb74fa0c08
Source dataset: uspto-grants-2014_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08884020B2

Reaction notes

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