Imidazole → HCID 56997753, compound

HRID 1584854Notes

Reaction equation

HRID 1584854 reaction equation
[OH:1][CH2:2][C:3]1[C:4]([CH2:11][CH3:12])=[N:5][C:6]([S:9][CH3:10])=[N:7][CH:8]=1.[Si:13](Cl)([C:16]([CH3:19])([CH3:18])[CH3:17])([CH3:15])[CH3:14].N1C=CN=C1>CN(C=O)C>[O:1]([CH2:2][C:3]1[C:4]([CH2:11][CH3:12])=[N:5][C:6]([S:9][CH3:10])=[N:7][CH:8]=1)[Si:13]([C:16]([CH3:19])([CH3:18])[CH3:17])([CH3:15])[CH3:14]

Participants

5

Reactant 3

HCID 795ImidazoleHCID 28928tert-Butyldimethylsilyl chlorideHCID 21220618HCID 21220618, compound

Product 1

HCID 56997753HCID 56997753, compoundYield 94%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of 5-hydroxymethyl-4-ethyl-2-methylthiopyrimidine (0.50 g, 2.72 mmol), t-butyldimethylsilylchloride (0.49 g, 3.26 mmol), and imidazole (0.20 g, 2.99 mmol) in DMF (5 mL) was stirred overnight and concentrated to give of 5-t-butyldimethylsiloxymethyl-4-ethyl-2-methylthiopyrimidine in a 94% yield (0.76 g); GC/MS calcd for C14H26N2OSSi (M+) 299, found 299. The title compound was then prepared by (a) oxidation of 5-t-butyldimethylsiloxymethyl-4-ethyl-2-methylthiopyrimidine (0.30 g, 1.0 mmol) with mCPBA (0.35 g, 2.0 mmol) as described for Example 67, (b) reaction with methyl hydrazine (0.16 mL, 3.0 mmol) followed by citraconic anhydride (0.11 g, 1.0 mmol) also described in Example 67; (c) reaction of 2-[N-(1'-aminocitraconamido)]-5-t-butyldimethylsiloxymethyl-4-ethylpyrimidine; (0.08 g, 0.21 mmol) and concentrated HCl (0.5 mL) in EtOH (20 mL) for 1 hour, concentration and chromatography (Hexanes/EtOAc, 2:1) to provide the title compound in 76% yield (0.043 g) from 2-[N-(1'-aminocitraconamido)]-5-t-butyldimethylsiloxymethyl-4-ethylpyrimidine; m.p. 108-110° C.

Workup

  1. concentrationconcentrated

Sources & evidence

ORD record
ord-666304a4e32348dba8678c751531c8ab
Source dataset
uspto-grants-1999_08
Patent number
US05935966

Reaction notes

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