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

HRID 914405Notes

Reaction equation

HRID 914405 reaction equation
C(N(CC)C(C)C)(C)C.[C:10]([O:14][C:15](=[O:28])[C:16]([S:19][C:20]1[S:21][CH:22]=[C:23]([CH2:25][CH2:26][NH2:27])[N:24]=1)([CH3:18])[CH3:17])([CH3:13])([CH3:12])[CH3:11].Cl[C:30]1[N:35]=[CH:34][C:33]([CH2:36][CH3:37])=[CH:32][N:31]=1>>[C:10]([O:14][C:15](=[O:28])[C:16]([S:19][C:20]1[S:21][CH:22]=[C:23]([CH2:25][CH2:26][NH:27][C:30]2[N:35]=[CH:34][C:33]([CH2:36][CH3:37])=[CH:32][N:31]=2)[N:24]=1)([CH3:18])[CH3:17])([CH3:11])([CH3:13])[CH3:12]

Participants

4

Reactant 3

HCID 81531DiisopropylethylamineHCID 35727632-Chloro-5-ethylpyrimidineHCID 597594492-{[4-(2-Aminoethyl)-1,3-thiazol-2-yl]thio}-2-methylpropionic acid tert-butyl ester

Product 1

HCID 597588712-[(4-{2-[(5-Ethylpyrimidin-2-yl)amino]ethyl}-1,3-thiazol-2-yl)thio]-2-methylpropionic acid tert-butyl esterYield 62.4%

Conditions

Temperature
130 °C

Procedure

N,N-Diisopropylethylamine (13.1 g) was added to 2-{[4-(2-Aminoethyl)-1,3-thiazol-2-yl]thio}-2-methylpropionic acid tert-butyl ester (27.9 g) synthesized in Example 7 and 2-chloro-5-ethylpyrimidine (13.2 g), and the mixture was stirred at 130° C. for 20 hr. The reaction mixture was directly purified by silica gel chromatography (elution solvent; hexane:ethyl acetate=2:1 to 1:1) to give the title compound (23.5 g) as a slightly yellow solid.

Workup

  1. customThe reaction mixture was directly purified by silica gel chromatography (elution solvent; hexane:ethyl acetate=2:1 to 1:1)

Sources & evidence

ORD record
ord-cadab0f0f8d248859be50302e666e404
Source dataset
uspto-grants-2011_09
Patent number
US08026370B2

Reaction notes

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