Isopropyl iodide → ethyl (RS)-2-[2-(2-methylprop-2-yl)-4-chloropyrimidin-5-yl]-3-methylbutyrate

HRID 34596Notes

Reaction equation

[Cl:1][C:2]1[C:7]([CH2:8][C:9]([O:11][CH2:12][CH3:13])=[O:10])=[CH:6][N:5]=[C:4]([C:14]([CH3:17])([CH3:16])[CH3:15])[N:3]=1.I[CH:19]([CH3:21])[CH3:20].C[Si]([N-][Si](C)(C)C)(C)C.[Li+]>>[CH3:17][C:14]([C:4]1[N:3]=[C:2]([Cl:1])[C:7]([CH:8]([CH:19]([CH3:21])[CH3:20])[C:9]([O:11][CH2:12][CH3:13])=[O:10])=[CH:6][N:5]=1)([CH3:16])[CH3:15]

Participants

Reactant 3

HCID 6362Isopropyl iodide

HCID 817777HCID 817777, compound

HCID 2733832Lithium Hexamethyldisilazide

Product 1

HCID 13911486ethyl (RS)-2-[2-(2-methylprop-2-yl)-4-chloropyrimidin-5-yl]-3-methylbutyrate

Procedure

4-chloro-5-ethoxycarbonylmethyl-2-(2-methylprop-2-yl)pyrimidine was reacted with 2-iodo-propane in the presence of lithium bis(trimethylsilyl)amide according to the procedure illustrated in example 6, to give ethyl (RS)-2-[2-(2-methylprop-2-yl)-4-chloropyrimidin-5-yl]-3-methylbutyrate.

Sources & evidence

ORD record: ord-274ef1521d5243b9a88c3ede58a9f262
Source dataset: uspto-grants-1988_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04762835

Reaction notes

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