2-Amino-5-methylthiazole → HCID 66660839, compound

HRID 556701Notes

Reaction equation

HRID 556701 reaction equation
[NH2:1][C:2]1[S:3][C:4]([CH3:7])=[CH:5][N:6]=1.[C:8]([NH:15][CH2:16][CH2:17][CH2:18]Br)([O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[O:9]>>[NH:1]=[C:2]1[N:6]([CH2:18][CH2:17][CH2:16][NH:15][C:8](=[O:9])[O:10][C:11]([CH3:14])([CH3:13])[CH3:12])[CH:5]=[C:4]([CH3:7])[S:3]1

Participants

3

Reactant 2

HCID 3517702-Amino-5-methylthiazoleHCID 4460490tert-butyl N-(3-bromopropyl)carbamate

Product 1

HCID 66660839HCID 66660839, compoundYield 70%

Conditions

Temperature
85 °C

Procedure

A mixture of 2-amino-5-methylthiazole (0.58 g, 5.0 mmol) and 3-(Boc-amino)propyl bromide (1.2 g, 5.0 mmol) was warmed to 85° C. and was allowed to stir for 4 h. The mixture was cooled to ambient temperature and was purified via column chromatography (SiO2, 9:1:0.1 CH2Cl2:methanol:ammonium hydroxide) to give the title compound (0.96 g, 3.5 mmol, 70% yield). MS (DCI/NH3) m/z 272 (M+H)+.

Workup

  1. temperatureThe mixture was cooled to ambient temperature
  2. customwas purified via column chromatography (SiO2, 9:1:0.1 CH2Cl2:methanol:ammonium hydroxide)

Sources & evidence

ORD record
ord-5364d36bc66b4730861e42e2c6da8653
Source dataset
uspto-grants-2011_11
Patent number
US08058293B2

Reaction notes

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