Diisopropylethylamine → 2-[(4-{[(5-Ethylpyrimidin-2-yl)amino]methyl}-1,3-thiazol-2-yl)thio]-2-methylpropionic acid tert-butyl ester

HRID 914503Notes

Reaction equation

HRID 914503 reaction equation
C(N(CC)C(C)C)(C)C.[C:10]([O:14][C:15](=[O:27])[C:16]([S:19][C:20]1[S:21][CH:22]=[C:23]([CH2:25][NH2:26])[N:24]=1)([CH3:18])[CH3:17])([CH3:13])([CH3:12])[CH3:11].Cl[C:29]1[N:34]=[CH:33][C:32]([CH2:35][CH3:36])=[CH:31][N:30]=1>>[C:10]([O:14][C:15](=[O:27])[C:16]([S:19][C:20]1[S:21][CH:22]=[C:23]([CH2:25][NH:26][C:29]2[N:34]=[CH:33][C:32]([CH2:35][CH3:36])=[CH:31][N:30]=2)[N:24]=1)([CH3:18])[CH3:17])([CH3:11])([CH3:12])[CH3:13]

Participants

4

Reactant 3

HCID 81531DiisopropylethylamineHCID 35727632-Chloro-5-ethylpyrimidineHCID 597590542-{[4-(Aminomethyl)-1,3-thiazol-2-yl]thio}-2-methylpropionic acid tert-butyl ester

Product 1

HCID 597591362-[(4-{[(5-Ethylpyrimidin-2-yl)amino]methyl}-1,3-thiazol-2-yl)thio]-2-methylpropionic acid tert-butyl esterYield 73.2%

Conditions

Temperature
130 °C

Procedure

N,N-Diisopropylethylamine (2.24 g) was added to 2-{[4-(aminomethyl)-1,3-thiazol-2-yl]thio}-2-methylpropionic acid tert-butyl ester (5.0 g) synthesized in Example 13 and 2-chloro-5-ethylpyrimidine (2.47 g), and the mixture was stirred at 130° C. for 8 hr. The reaction mixture was directly purified by silica gel chromatography (elution solvent; hexane:ethyl acetate=1:1) to give the title compound (5.0 g) as a slightly yellow oil.

Workup

  1. customThe reaction mixture was directly purified by silica gel chromatography (elution solvent; hexane:ethyl acetate=1:1)

Sources & evidence

ORD record
ord-0c3ecc05789a4bf8b11d4e8267d9d8f4
Source dataset
uspto-grants-2011_09
Patent number
US08026370B2

Reaction notes

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